All Episodes

Jen & Tim Show: Tasty Limbo

Trump Toohey: Who is Harrison Ford’s wife?

Jen & Tim Show: Bus Chat

Trump Toohey: Who has more followers on Instagram? Karol G or Bruno Mars?

Jen & Tim Show: Nate’s Mom Gets an Upgrade As The Mattress Saga Continues...

Trump Toohey: What is the name of Selena Gomez's beauty line?

Jen & Tim Show: TSA is cracking down on what?

Trump Toohey: In the song “Baby Shark” we start with mention of Baby Shark, then Mommy Shark and onto Daddy Shark. Which shark is mentioned next?

Trump Toohey: The Cavs current social media pages support the new WNBA team in town. What is their name?

Jen & Tim Show: Too Good To Go

Trump Toohey: Which Cleveland Brown was on the cover of “Madden 12” which was released in 2011?

Jen & Tim Show: It was Tim's fault

Trump Toohey: What is the name of the reality show that stars Brooks Nader alongside her 3 sisters?

Trump Toohey: Coco Jones has a Grammy for best R&B Solo performance for which song?

Jen & Tim Show: Mini Van Monday

Trump Toohey: Which Harry Potter film was released the year after 'Harry Potter and the Sorcerer’s Stone'?

Trump Toohey: The people who drive and work on the Oscar Meyer Wienermobile are officially called what?

Jen & Tim Show: Chicken tender basket with gravy

Trump Toohey: What was the name of the Cleveland Rockers' mascot?

Jen & Tim Show: Throwing it back to 2006

Trump Toohey: What is the food item in that deli IKEA is famous for serving?

Jen & Tim Show: Delays are the new norm

Trump Toohey: Who is Josh Allen’s wife?

Jen & Tim Show: Money Monday

Trump Toohey: What was the previous name of Steel Vengeance prior to an entire remodel and rebrand in 2018?

Trump Toohey: What classic story features Ebenezer Scrooge?

Jen & Tim Show: How much is your electric bill!?

Trump Toohey: What is the name of the couple that just won 'Love Island USA' Season 8?

Trump Timmay: Which lifestyle icon has co-hosted cooking shows and specials with Snoop Dogg?

Trump Toohey: Which K-pop group is JENNIE a member of?

Jen & Tim Show: Right Eyed Richards

Trump Timmay: Name one of the four original Bratz doll character

Trump Toohey: Zoë Saldaña is most known for her role in which popular science fiction film series?

Trump Toohey: What is the name of the popular girls' clique Jenna wants to join in the original film ’13 Going on 30’?

Jen & Tim Show: One Star Wednesday

Trump Toohey: What is the name of Ella Langley’s song that is currently #1 on the Billboard Hot 100 chart?

Jen & Tim Show: Jen's Big Return

Trump Toohey: The primary antagonist of the A Nightmare on Elm Street franchise is who?

Trump Toohey: What is the name of Barbie's younger sister introduced in 1964?

Jen & Tim Show: Ocular Event

Trump Toohey: Name at least one of the four original Cheetah Girls

Jen & Tim Show: Do you wash your dogs food bowl?

Trump Toohey: Jack Antonoff was in which band from 2008-2015?

Jen & Tim Show: Fluffing Out & Wedding Costs

Trump Toohey: Hilary Duff became famous in the early 2000s for her role in which Disney Channel series?

Jen & Tim Show: Bucket and Chuck It

Trump Toohey: Sean Penn recently won an Academy Award for “Best Supporting Actor” for which 2025 film?

Trump Toohey: What is the signature private-label brand at Costco?

Jen & Producer Stevie Unpack the Taylor Swift and Travis Kelce Wedding Rumors

Trump Toohey: Which hit Netflix series featured Ruby Rose as a prisoner named Stella?

Trump Toohey: What 2004 romantic comedy featured Jennifer Garner as Jenna Rink?

Trump Toohey: Jeremy Renner portrayed which character in the Marvel Cinematic Universe?

Jen & Tim Show: It's a 90's summer!

Jen & Tim Show: Stevie's Secret Mission

Trump Toohey: “Dutton Ranch” is a spinoff of which show that ran from 2018-2024?

Jen & Tim Show: Spoiler Spouse

Trump Toohey: The first ever celebrity Barbie doll was based on which British supermodel from 1967?

Jen & Tim Show: What is that sound!?

Trump Toohey: What is the name of the cowgirl in the Toy Story franchise?

Trump Toohey: In which museum-themed movie franchise does Ben Stiller play Larry Daley?

Jen & Tim Show: Traveling Dentist

Trump Toohey: Which television series did Eugene Levy create alongside his son Dan Levy?

Jen & Tim Show: MMMaley's

Trump Toohey: New episodes of “Love Island USA” can be found exclusively on which streaming platform?

Jen & Tim Show: Squats and Lunges

Trump Toohey: Bridgit Mendler starred in which Disney Channel sitcom as Teddy Duncan?

Jen & Tim Show: Numbed & Dilated

Trump Toohey: What is the name of Moana's signature song about wanting to explore beyond her island?

Jen & Tim Show: Envelope Dream

Trump Toohey: What breed of dog is Scooby-Doo?

Jen & Tim Show: Wheels Down & WaterDash

Trump Toohey: Ethan Slater played which role in Wicked?

Trump Toohey: What is the name of Elton John and Dua Lipa’s 2021 dance track?

Trump Toohey: In the 'Toy Story' films, what is the name of Woody's horse?

Jen & Tim Show: Birthday Bucket List

Trump Toohey: Sara Bareilles wrote the music and lyrics for which Broadway musical?

Jen & Tim Show: Name that Bird

Trump Toohey: Nicholas Hoult famously played which role in last year’s “Superman”?

Jen & Tim Show: Dot-free Dot Cake

Trump Toohey: Who is Myles Garrett's Olympic gold medal winning girlfriend?

Jen & Tim Show: The Wipers of the House

Trump Toohey: Which 2011 song by Jennifer Lopez is going viral thanks to the young adult romance series Off Campus?

Jen & Tim Show: Fancy Field Report

Trump Toohey: What is Guy Fieri’s signature catchphrase about exciting food destinations?

Jen & Tim Show: Chunk of bugs

Trump Toohey: What was the name of the street in which the center of the drama on “Desperate Housewives” takes place?

Jen & Tim Show: FroYo and a Matinée

Trump Toohey: Russell Crowe played the role of “Maximus” in which 2000 film?

Trump Toohey: What nickname is Grogu most commonly known by?

Dom Russo’s sister shares what she believes happened in the car, whether she’ll speak to Mackenzie again, and how she’s keeping Dom’s legacy alive

Trump Toohey: The regulation distance for the Daytona 500, NASCAR’s biggest race, is how many laps?

Jen & Tim Show: Say 'Au Revoir'

Jen & Tim Show: When is your kiddos last day of school!?

Trump Toohey: Joey Chestnut’s record in the contest is how many hot dogs and buns eaten in 10 minutes?

Jen & Tim Show: What happened last night!?

Trump Toohey: Approximately how many chips are in a standard can of Pringles?

Jen & Tim Show: A Scoop Squad minor issue

Trump Toohey: What television series featured Gwyneth Paltrow as substitute teacher Holly Holliday?

Jen & Tim Show: Fragrance Friday

Trump Toohey: What is the name of Ash’s hometown in Pokémon?

Jen & Tim Show: Man Pregnant

Trump Toohey: What TV series made Shailene Woodley widely known as a teenager?

Jen & Tim Show: Cream Team or Scoop Squad?

Trump Toohey: Nicole Williams English really rose to prominence starring in which reality show that aired on E!?

Jen & Tim Show: Gettin' Dirty

Trump Toohey: What is the last name of the family featured in the 'Little House On The Prairie'?

Jen & Tim Show: Stevie's new alarm clock

Trump Toohey: Anya Taylor-Joy starred in which 2020 Netflix series as a chess prodigy?

Jen & Tim Show: Snack Driven Man

Trump Toohey: Which Minion often acts like the leader of the group?

Jen & Tim Show: Smells like toes

Trump Toohey: Thursday, May 7, 2026

Jen & Tim Show: This show has issues

Trump Toohey: What is the title of Stevie Nicks’ debut solo album?

Jen & Tim Show: The Pokey Pen and Clicking Thing

Trump Toohey: Benji Madden is best known for co-founding which rock band with his identical twin brother Joel?

Jen & Tim Show: Stranded by Spirit

Trump Toohey: What magical object allows the Pevensie children to enter Narnia?

Trump Toohey: The People's Prize has been CLAIMED and Jen had her 600th LOSS!

Jen & Tim Show: We are BACK from Jamaica! Tim almost didn't make it home...

An All-Inclusive Music Festival in Jamaica is a THING!

Jen & Tim talk snakes and going on ATV's in Jamaica

The Hotel Manager of Beaches Negril joined Jen and Tim to talk food and entertainment

Jen & Tim talk with Fiona about Jamaican tourism and the beautiful sunsets

Jen & Tim live in Jamaica talking food & culture

Trump Toohey: Maura Higgins gained stardom from which reality show about finding love?

Jen & Tim Show: Passport Drama

Trump Toohey: Over or under 15 Grammy wins for Alicia Keys?

Jen & Tim Show: Are you a Jen or a Tim?

Trump Toohey: Name the primary fragrance launched under Kylie Jenner's brand, which debuted in 2024.

Jen & Tim Show: Stevie's Major/Minor Problems

Trump Toohey: Christina Applegate's last major acting role is her starring performance as Jen Harding in the which Netflix series that ended in 2022?

Jen & Tim Show: Our boss has an announcement for us...

Trump Toohey: Which state would you find Coachella?

Jen & Tim Show: Our boss has some news for us...

Trump Toohey: What did Snoop Dogg change his name to in 2012?

Jen & Tim Show: The Whale Fall

Trump Toohey: What is the name of the hotel manager in Season 1 of “The White Lotus”?

Jen & Tim Show: Tube of Chocolate

Trump Toohey: Jonathan Groff voiced the character Kristoff in which Disney animated film series?

Trump Toohey: Nick Jonas is set to star in a new untitled Netflix romantic comedy marking his latest move in an increasingly busy film career. Jonas is also set to reprise his role in this franchise of films later this year, alongside Dwayne Johnson?

Jen & Tim Show: The swings, the pars and the birdies

Trump Toohey: Who won last season of American Idol?

NASA's Darcy DeAngelis talks all things Artemis

Jen & Tim Show: First Job Friday

Trump Toohey: Which U.S. state is famous for loving Jell-O so much it made it an official snack?

Jen & Tim Show: Parking meter drama is back

Trump Toohey: Which political drama series did Michael J. Fox star in during the 1990s?

Jen & Tim Show: Watch List

Trump Toohey: How many kids does Meryl Streep have?

Jen & Tim Show: Should Tim get a Hello Fresh subscription?

Trump Toohey: What 2007 musical comedy film featured Amanda Bynes alongside Zac Efron and Nikki Blonsky?

Jen & Tim Show: Pothole Patrol

Trump Toohey: Which crime drama is Shemar Moore best known for starring in as Derek Morgan?

Jen & Tim Show: Guards Home Opener and Final Fish Fry Friday

Trump Toohey: John Travolta played the role of Danny Zuko in which 1978 Musical/Comedy film?

Jen & Tim Show: The Producer vs. The Pothole

Trump Toohey: Madelyn Cline is known for her role in which Netflix original teen drama?

Jen & Tim Show: Dental Update

Trump Toohey: Which 2022 song helped Noah Kahan gain major popularity on social media?

Jen & Tim Show: Where do you hide food?

Trump Toohey: What is the first name of the character played by Eric Dane on 'Euphoria'?

Jen & Tim Show: Roll It Back Up!

Trump Toohey: What platform at King’s Cross Station does the Hogwarts Express depart from?

Jen & Tim Show: We are ancient

Trump Toohey: Pamela Anderson starred in which series about lifeguards who patrol beaches in LA?

Jen & Tim Show: Have you ever been called the wrong name?

Trump Toohey: Which hit TV show made Lea Michele famous?

Jen & Tim Show: Know the Show

Trump Toohey: What Disney Channel show did Dylan Sprouse star in with his twin brother Cole?

Jen & Tim Show: Colonel's Favorite Jellybean

Trump Toohey: One of Jessica Biel's biggest roles includes her role as Mary Camden on which show?

Jen & Tim Show: The Match

Trump Toohey: Simon Baker is best known for his role in which show that ran for 7 seasons on CBS?

Jen & Tim Show: Fragment Friday

Trump Toohey Redemption Week: Elaine and Jon

Jen & Tim Show: What is Liu?

Trump Toohey Redemption Week: Jackie and Shaun take on Jen in studio

Jen & Tim Show: THE BIG BOOM!

Trump Toohey Redemption Week: Lisa and Mason

Jen & Tim Show: Rough Beef

Trump Toohey: Day 2 of Redemption Week with Kayla of Perry and Sarah of Parma Heights

Jen & Tim Show: What's in the box!?

Trump Toohey: Redemption Week Day 1 with Ivanne and Nancy!

Trump Toohey: A sweet tribute in the Osbourne family. Jack Osbourne and his wife have welcomed a baby girl and named her Ozzy Matilda, honoring his late father, rock legend Ozzy Osbourne. Ozzy’s wife, Sharon, was a judge on two talent competition shows.

Trump Toohey: Pop star Harry Styles is building buzz around his new album, Kiss All The Time, Disco Occasionally, which was released last week. In 2023, Styles won album of the year at the Grammy awards for which album?

Trump Toohey: Katherine Heigl made her first public appearance in two years at a charity fundraiser. The actress previously mentioned life away from the spotlight has brought her “peace” and “joy”. What was the first name of her character’s name on Grey’s

Trump Toohey: Cleveland Heights native Travis Kelce is expected to return to the Chiefs - this will be his 14th NFL season. What’s the name of the podcast he co-host with his brother?

Trump Toohey: Saks was one of the two anchor stores at Beachwood place when it opened in 1978. What was the other store?

Trump Toohey: What is the name of the iconic bag behind designer Chloé?

Jen & Tim Show: Refuse the cruise

Jen & Tim Show: Jen's packing guide

Trump Toohey: Which pop star was Josh Duhamel married to from 2009 to 2019?

Jen & Tim Show: March It Up!

Trump Toohey: Beyhive refers to the fans of which female artist/singer?

Jen & Tim Show: Clone or Carrey?

Jen & Tim Show: Water Hole to Water Hole

Trump Toohey: In 2024, Paul Mescal starred in the sequel to which epic historical film?

Jen & Tim Show: Dirty Mouth, Dirty Feet

Trump Toohey: Who were two of the main cast members from Season 1 of Laguna Beach?

Jen & Tim Show: Wu-Tang Clan and INXS

Trump Toohey: Donovan Mitchell is engaged to which Grammy-winning singer and actress?

Jen & Tim Show: Bird Bracket

Trump Toohey: Harry Potter was sorted into which house at Hogwarts?

Jen & Tim Show: Flock Fail

Trump Toohey: Harry Styles’ acting career includes an appearance in which Oscar winning film directed by Christopher Nolan?

Jen & Tim Show: Goose Springsteen, Winnie and Miss. Vickie

Trump Toohey: What are Barry Manilow fans called?

Jen & Tim Show: Seat of anxiety

Trump Toohey: What is the name of the spork character that was introduced in “Toy Story 4”?

Jen & Tim Show: Airport Theory

Trump Toohey: Does Kristen Bell voice Anna or Elsa in the “Frozen” films?

Jen & Tim Show: Pączki Problems

Trump Toohey: Which Hemsworth brother plays the role of Thor?

Jen & Tim Show: Built Different

Trump Toohey: Which award-winning dystopian series became one of Hulu’s first major originals?

Jen & Tim Show: Who stole Producer Stevie's snacks!?

Trump Toohey: What movie did Harry Styles star in alongside Florence Pugh in 2022?

Jen & Tim Show: What is the point of a long-stem rose?

Trump Toohey: The series ‘XO, Kitty’ is a spin-off of which popular romance Netflix film series?

Jen & Tim Show: McDonald’s Caviar and Minty Goodness

Trump Toohey: Brendan Fraser has an Oscar for “Best Actor” for which 2022 film?

Jen & Tim Show: What's in the crack?

Trump Toohey: What clip-based comedy show did Bob Saget host?

Jen & Tim Show: Chesty and Browy

Trump Toohey: Which 2005 comedy stars Rachel McAdams alongside Owen Wilson and Vince Vaughn?

Trump Toohey: What is Captain Jack Sparrow’s ship called?

Trump Toohey: Who won 'The Voice' Season 3 and later appeared on Broadway?

Trump Toohey: Which male artist took home the Best New Artist award at the Grammys in 2017?

Trump Toohey: Who was the head coach of the Cleveland Cavaliers in 2016 when they won the championship?

Jen & Tim Show: Bowl in the Hole

Trump Toohey: Which popular Netflix dating show features singles dating in pods unable to see each other?

Jen & Tim Show: Pogoliers

Trump Toohey: Which popular TV series did Lainey Wilson appear in as a recurring character?

Jen & Tim Show: Ocular Superhero and Snow Day Drama

Trump Toohey: Quinta Brunson plays the role of Janine in which sitcom?

Jen & Tim Show: Bed bugs of the snow

Trump Toohey: Which musical received the most Tony nominations ever?

Jen & Tim Show: Watch out for exploding trees!!

Trump Toohey: Nicholas Galitzine starred in the film ‘The Idea of You’ alongside which famous actress?

Jen & Tim Show: We play dumb games

Trump Toohey: What fashion magazine did Harry Styles become the first solo male cover star of?

Jen & Tim Show: Head Hole and a Neck Cave

Trump Toohey: Martin Short appears in Santa Clause 3 as which antagonist trying to take over Christmas?

Jen & Tim Show: Soup You Can Suck!

Trump Toohey: What is the name of Lizzie McGuire's nerdy but loyal best friend?

Jen & Tim Show: Neighbor Number 102

Trump Toohey: Which girl group sang the song “I’m In Love With a Monster” for the soundtrack to Hotel Transylvania 2?

Jen & Tim Show: Great day for a heated blanket!

Trump Toohey: Fans of Jason and Travis Kelce’s podcast are called what?

Jen & Tim Show: Heated and Sheeted

Trump Toohey: What is the first name of the character Kaley Cuoco played in 'Big Bang Theory'?

Jen & Tim Show: Don't need to scrub them to love them

Trump Toohey: What is the Apple TV sitcom series about a soccer coach called?

Jen & Tim Show: Jen the Brick

Trump Toohey: Ariana Grande is known for which signature hairstyle early in her career?

Jen & Tim Show: Tim is judging Jen for her latest purchase

Trump Toohey: Nikki Glaser was born in which city in Ohio?

Jen & Tim Show: Snow blowing drama

Trump Toohey: Which Girl Scout cookie is described as a crispy cookie layered with peanut butter and covered with a chocolaty coating?

Jen & Tim Show: It's baaaaaack!

Trump Toohey: Which actress stars alongside Sydney Sweeney in ‘The Housemaid’ as the character Nina?

Jen & Tim Show: Air fryer hacks

Trump Toohey: Which day in 1983 did Will Byers vanish?

Jen & Tim Show: The door is ajar

Trump Toohey: What is the name of Hannah Montana’s bodyguard in the show?

Trump Toohey: What is the name of Beyoncé’s athleisure clothing line that has had partnerships with brands like Adidas?

Trump Toohey: What is the name of Dunkin’s bite-sized donut holes?

Lunar Family Lights, winners of 'The Great Christmas Light Flight' in Willoughby, talk why they had to close early

Trump Toohey: What do creators receive when they hit 100,000 subscribers on YouTube?

Trump Toohey: What character does Finn Wolfhard play on Stranger Things?

Jen & Tim Show: Hairy Flour

Trump Toohey: Which popular Christmas song features Ariana Grande singing with Kelly Clarkson?

Jen & Tim Show: Why didn't the handle pull down work?

Trump Toohey: In the song “Gaston”, what is one thing that no one does like Gaston?

Jen & Tim Show: Do you keep presents under the tree early?

Trump Toohey: What long-running HGTV series follows homebuyers choosing between three homes?

Jen & Tim Show: Jen got her 2,000th win in Trump Toohey! What did Tim get her to celebrate?

Trump Toohey: What 2015 romantic comedy starred Amy Schumer as a commitment-phobic journalist?

Jen & Tim Show: Tim went shopping, but didn't know it

Trump Toohey: Demi Lovato starred alongside Selena Gomez in which 2009 Disney channel movie?

Jen & Tim Show: Jen's Pinterest fail

Trump Toohey: What is the name of Blake Lively’s character on Gossip Girl?

Jen & Tim Show: White Elephant Gift Ideas

Trump Toohey: Howie Mandel is most notably known for hosting which game show?

Jen & Tim Show: Does Tim have dirty socks?

Trump Toohey: Which fast food company collaborated on a special meal with 'Five Nights at Freddy’s'?

Jen & Tim Show: Santa Claus is coming to…. the studio!

Trump Toohey: What city does Kevin accidentally fly to in 'Home Alone 2'?

Jen & Tim Show: Will the annual Christmas Card be ready in time!?

Trump Toohey: What actress plays the role of ‘Emily’ in Emily in Paris?

Trump Toohey: What is the name of Clark’s cousin who shows up uninvited in 'National Lampoon’s Christmas Vacation'?

Trump Toohey: Millie Bobby Brown and Noah Schnapp are co-stars on which popular Netflix original series?

Trump Toohey: What is the name of the rabbit police officer in Zootopia?

Trump Timmay: Which 2001 romantic comedy starred Jennifer Lopez opposite Matthew McConaughey?

Jen & Tim Show: Holiday Travel Debate

Trump Timmay: What is the name of the sci-fi film that Glen Powell stars in as Ben Richards?

Trump Timmay: What streaming service would you find 'Beast Games' on?

Jen & Tim Show: CHRISTMAS MUSIC IS HERE!

The FINAL Day of Trump Toohey Redemption Week with Angelina and Alecia!

Jen & Tim Show: Jen has a Wicked problem

Trump Toohey: Jen tried to get redemption on Mary and Lisa. How did she do?

Jen & Tim Show: TikTok Junk

Trump Toohey: What is the name of the spinoff movie focused on Ashley Tisdale’s ‘High School Musical’ character?

Jen & Tim Show: We drank expired hot chocolate

Trump Toohey redemption week continues with Lori, John & his son Michael with back-to-back losses for Jen

Jen & Tim Show: Did you get 10-4'ed!?

First Day of Trump Toohey Redemption Week with Emily and Janet!

Jen & Tim Show: Selfies with Stevie

Trump Toohey: Boston Rob is best known for his time on which reality competition show?

Jen & Tim Show: Red Cup Drama

Trump Toohey: Meghan Trainor is married to Daryl Sabara, an actor known for his role in which franchise of films?

Jen & Tim Show: Netflix of the Mouth

Trump Toohey: Brittany Snow gained recognition from 1998-2001 for her role in which CBS Soap Opera?

Jen & Tim Show: Dupe-ish

Trump Toohey: What Nickelodeon TV show made Leon Thomas widely known to teen audiences?

Trump Toohey: What 2015 TV series marked Hilary Duff’s return to acting as Kelsey Peters?

Jen & Tim Show: Sunburn, UFO or caveman?

Jen & Tim Show: Shopping with Jen!

Trump Toohey: Shay Mitchell is best known for her role as Emily in which 2010 drama series?

Jen & Tim Show: Bailey or Brady?

Trump Toohey: What 2019 film earned Adam Sandler critical acclaim for his dramatic performance?

Jen & Tim Show: Handy Light

Trump Toohey: What Disney Channel show made Hilary Duff a household name?

Jen & Tim Show: Plain Bird and Potatoes

Trump Toohey: What is the name of the MTV show starring host Rob Dyrdek with his bodyguard?

Jen & Tim Show: We have a WINNER for Dead Guy In An Envelope!

Trump Toohey: Halloween Edition!

Jen & Tim Show: What can Aunt Jen do for you?

Trump Toohey: When saying “6-7” you also make a motion with which part of your body?

Jen & Tim Show: Another Producer Stevie tire update...

Trump Toohey: What was Al Bundy’s job on ‘Married with Children'?

Jen & Tim Show: Why do SO many people text THEMSELVES!?

Trump Toohey: What is the Pillsbury Doughboy’s official name?

Jen & Tim Show: Spookley the Square Pumpkin

Jen & Tim Show: Foo's or Goo's?

Jen & Tim Show: Should you quit your day job?

Trump Toohey: Bon Jovi was inducted into the Rock and Roll Hall of Fame by which long running shock jock that has been on SiriusXM for years?

Trump Toohey: Stevie Nicks is often nicknamed the “Queen of” what?

Trump Toohey: Stevie Nicks is often nicknamed the “Queen of” what?

Jen & Tim Show: Attack that bag

Trump Toohey: Which of the 4 theme parks at Disney World would you find the Soarin’ Ride?

Jen & Tim Show: Who even drinks a Whiskey Sour!?

Trump Toohey: Which state has the highest population? California or Texas?

Jen & Tim Show: Squeaky Shoes

Trump Toohey: Colin Jost has been married to which actress since 2020?

Jen & Tim Show: You can't backflip your way out of this one…

Trump Toohey: What is the name of the Holiday Rom-Com released on Netflix last year about a snowman coming to life?

Jen & Tim Show: Clammy Cleveland

Trump Toohey: What was the characters name that Lisa Ann Walter played in the 1998 film 'The Parent Trap'?

Jen & Tim Show: Dumpster buddies

Trump Toohey: What song did Demi Lovato release in 2013 that became one of her biggest hits and her second top-ten single on the Billboard Hot 100?

Jen & Tim Show: Turnpike drama

Trump Toohey: Diane Keaton starred alongside Steve Martin in which 1991 family comedy movie?

Jen & Tim Show: When can Tim open the box?

Trump Toohey: What is the name of the Rupunzel’s kingdom?

Jen & Tim Show: Pick Your Park(s)

Today's contestant during 'Cleveland, How Much Do You Make?' was a Logistics Technician

Trump Toohey: Ryan Murphy created which medical drama television series that ran from 2003 to 2010?

Jen & Tim Show: Tim's karma

Trump Toohey: How many letters are in each Wordle puzzle answer?

Jen & Tim Show: Tim has a surprise for Jen

Trump Toohey: What is the name of Ed Sheeran’s latest album released just weeks ago?

Jen & Tim Show: What was THAT!?

Trump Toohey: What is the name of the sarcastic and often mean attending doctor who mentors J.D. in the show 'Scrubs'?

Jen & Tim Show: Time to pay our dues…

Trump Toohey: What is the name of those charms you can easily add to Crocs?

Jen & Tim Show: Halloween Costumes & Bad TV Show Recommendations

Today's contestant during 'Cleveland, How Much Do You Make?' works as a Software Director

Trump Toohey: What is the name of Charlie Brown’s little sister?

Jen & Tim Show: Whip cream to the face

Trump Toohey: What type of bear is most commonly found in North America?

Cleveland, How Much Do You Make: Today's contestant works in Admissions Marketing

Trump Toohey: What is the name of the 2008 romance/drama film starring both Scarlett Johansson and Natalie Portman?

Jen & Tim Show: Timmy the Tiger

Trump Toohey: Selena Gomez voiced the character Mavis Dracula in which popular animated film series?

Jen & Tim Show: Tuna on a plane

Trump Toohey: Years ago on “The Muppets”, what was the name of the scientist who often worked with Beaker?

Jen & Tim Show: Bony the Rooster has been leashed

Cleveland, How Much Do You Make: Today's contestant has worked in construction for 43 years

Trump Toohey: Which famous supermodel was one of the first big faces of Maybelline in the 1990s?

Jen & Tim Show: We don’t know our fruits

Trump Toohey: What was Rihanna’s first U.S. number-one single on the Billboard Hot 100, back in 2006?

A Firefighter Lieutenant played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: In the 2023 live-action The Little Mermaid, which Disney villain did Melissa McCarthy play?

Jen & Tim Show: Stevie the Shaver

Trump Toohey: Approximately how many liters of beer are consumed during Oktoberfest each year?

Jen & Tim Show: Milky the Cow

Trump Toohey: Dolly Parton was inducted into the Rock and Roll Hall of Fame in 2022 by which pop star?

Trump Toohey: In a standard game of Battleship, which ship is the smallest needing only two hits to sink?

Jen & Tim Show: The Browns Beard

Trump Toohey: Which show that was a big winner from Sunday night’s Emmys can be found on HBO Max?

A Product Developer played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Mariah Carey starred in which 2001 film loosely based on her career?

Jen & Tim Show: Something stinks…

Trump Toohey: Which Ariana Grande song spent seven weeks at No. 1 on the Billboard Hot 100 in 2019?

Jen & Tim Show: Apparently, you DON'T have to pay speeding tickets!?

Trump Toohey: Which famous actor plays the role of “The Penguin” in the TV series?

Trump Toohey: What instrument does Wednesday play throughout the series?

Trump Toohey: Which 2003 Hilary Duff film features her looking identical to a famous pop star in Rome?

Trump Toohey: Josh Dun is the drummer for which band from Columbus, OH?

Trump Toohey: Which two artists are currently tied for the most MTV Video Music Awards of all time, with 30 wins each?

Jen & Tim Show: Jen hates autopay

Trump Toohey: What breed of dog is Bluey?

Jen & Tim Show: The Cleveland Hole

Trump Toohey: The first ever winner of DWTS was which actress?

A Public Administrator Plays 'Cleveland, How Much Do You Make?'

Jen & Tim Show: Lock the door shows

Trump Toohey: Which war is the setting of the very first Call of Duty?

Trump Toohey: Jaws was what type of shark?

Trump Toohey: There’s a new Skelly in town - and this one is from Lowes. Remember we talked about the 12 foot Home Depot one? Well, Lowe’s has introduced theirs, and it’s a 20 foot inflatable that will cost you $269. Which month is Halloween?

Operations Manager at a Manufacturing Facility Plays 'Cleveland, How Much Do You Make?'

Trump Toohey: Billie Eilish dropping her very own “UNO Canvas Billie Eilish” deck, now up for pre-order on her site. In the game of UNO, how many cards are initially dealt to each player?

Trump Toohey: Taylors Version -- Travis initially tried to give Taylor Swift something at her concert that went viral. What was it?

Trump Toohey: Austin Butler was nominated for an Oscar for Best Actor for his portrayal of Elvis, but lost to Brendan Fraser for his role in which film?

Jen & Tim Show: Wheelies Down the Highway

Trump Toohey: Which 2019 monster movie featured Millie Bobby Brown as Madison Russell?

Jen & Tim Show: Misty in Mentor

Trump Toohey: Carly Rae Jepsen first rose to fame after placing third on what Canadian singing competition show?

The First EVER Jen and Tim Show Wood Quiz!

Jen & Tim Show: Hug, drink and muffins

Jen & Tim Show: Bloody Cookies & Fat Boy Sandwiches

A Carpentry Apprentice Played 'Cleveland, How Much Do You Make?'

Trump Toohey: Sabrina Carpenter voiced Princess Vivian on which Disney Junior animated series?

Jen & Tim Show: Cockroach to the neck

Trump Toohey: Jared Leto won an Academy Award for Best Supporting Actor for which 2013 film?

Trump Toohey: What is the name of Vans’ skateboarding competition and music festival that began in 1995?

Trump Toohey: What is the name of Snoopy’s yellow bird friend?

Trump Toohey: What Netflix movie made Noah Centineo a breakout star in 2018?

Trump Toohey: Which former SNL cast member went on to star in the Wayne’s World movies as Wayne?

Trump Toohey: What is the name of the evil ventriloquist dummy in many 'Goosebumps' books?

A Customer Service Representative played 'Cleveland, How Much Do You Make?'

Trump Toohey: Which movie earned Jordan Peele an Academy Award for Best Original Screenplay?

Trump Toohey: In the lullaby “Rock-a-Bye Baby,” where is the cradle located?

Trump Toohey: The main ranking system on Rotten Tomatoes is called what?

Trump Toohey: Who is the lead singer of Maroon 5?

Trump Toohey: Justin Timberlake’s 2003 song ‘Cry Me a River’ is rumored to be about his breakup with which popstar?

Trump Toohey: Dwayne ‘The Rock’ Johnson played a girl dad/ football star in which 2007 family comedy?

Jen & Tim Show: Expensive honeymoons & Jen's crazy packing hack

Trump Toohey: Adam Sandler’s highest grossing non-animated movie of all time, was which 2010 film?

Jen & Tim Show: Is Jen a Utah Mom?

A Communications Administrator played 'Cleveland, How Much Do You Make?'

Trump Toohey: Which TV dance competition show helped launch Tate McRae’s career back in 2016?

Jen & Tim Show: What do you do if you HATE your engagement ring?

Trump Toohey: What was the name of the character Adam Sandler played during his time on SNL who sang the news using Italian words?

Jen & Tim Show: Stamp Chat

Trump Toohey: Which city is the home of Browns training camp?

Jen & Tim Show: Browns making a splash and a Hopkins Hangout Pass

A Licensed Practical Nurse played 'Cleveland, How Much Do You Make?'

Trump Toohey: Which Midwest city is home to O’Hare International Airport?

Jen & Tim Show: Bony Rooster

Trump Toohey: What is the name of the popular ‘Breaking Bad’ spinoff prequel series?

Jen & Tim Show: Jen and the Dragons

A forklift operator played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Jennifer Lopez was a backup dancer on which TV show before becoming a singer and actress?

Jen & Tim Show: Tim got 'jumped' in Times Square

Trump Toohey: What’s the name of the 2014 hit song by Iggy Azalea that featured Charli XCX?

Trump Toohey: Scarlett Johansson plays the lead role of Zora Bennett in which action film in theatres now?

Trump Toohey: Which actress earned an Oscar for her lead role in Black Swan?

Jen & Tim Show: Mom Dating and Guac-a-Mouth

Trump Toohey: James Blunt is best known for his 2004 breakout hit single titled what?

Jen & Tim Show: If you're engaged, are you off the market?

Trump Toohey: Which actor played the role of Harry Potter in all 8 of the films in the series?

Jen & Tim Show: Tim was right for the first time ever and a Superman review

Trump Toohey: Which country was Season 7 of Love Island filmed?

Jen & Tim Show: Cleveland is Metropolis

Trump Toohey: What is the name of the fictional hospital in the series Scrubs?

Jen & Tim Show: Wedding Drama and Superman

Trump Toohey: Which WNBA team does Angel Reese play for?

Jen & Tim Show: Fecal Beach and Poop Show

Trump Toohey: What is the name of Garfield’s yellow beagle best friend?

Jen & Tim Show: Age, Weight, Birthday

A Veterans Success Coach played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Which movie, based on a Nintendo game, was a huge smash at the box office in 2023?

Jen & Tim Show: Two claws, two pretzels at Cedar Point

Trump Toohey: What is Ozzy Osbourne’s real first name?

Jen & Tim Show: Jen's husbands has a heavy box. What is in it?

A truck driver played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Which famous duet partner joined Barbra Streisand on the hit song “Tell Him” in 1997?

Jen & Tim Show: Hiccup help and glass fruit cutting

Trump Toohey: Which actor plays the main character/chef in the series The Bear?

Jen & Tim Show: Hot dog of the sea

Trump Toohey: Who holds the record for most points in WNBA history?

Jen & Tim Show: Bloom, Brady or Bezos?

Trump Toohey: What is the name of the car the T-Birds fix up in the film Grease?

Jen & Tim Show: OHHH MAAMMMAAAAA!!

Trump Toohey: Who is Keith Urban’s wife?

Jen & Tim Show: Long or short hair?

Trump Toohey: Ron Howard has an Academy Award for Best Director and Best Picture for which 2001 film?

A nurse in the ICU played a round of 'Cleveland, How Much Do You Make?'

Jen & Tim Show: Butter Break Down and Poop Cruise

Trump Toohey: Shane Gillis currently starts in which hit show series that is currently in the top 10 on Netflix?

Jen & Tim Show: Shaking our own butter

A HR Generalist for a manufacturing company played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What type of steak is traditionally used in a Philly cheesesteak?

Jen & Tim Show: Tim is back and he has a surprise for Producer Stevie

Trump Toohey: How many members make up the boy band BTS?

Trump Toohey: What video-sharing platform does MrBeast primarily use and is the most subscribed individual on?

Trump Toohey: What do the letters in the game MASH stand for?

Trump Toohey: What MTV reality show made Mike "The Situation" famous?

Trump Toohey: In the series Dr. Who, what is the Doctor’s time-traveling ship famously disguised as?

Jen & Tim Show: Meat-It

An IT Analyst played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What Nickelodeon game show involved getting slimed and answering trivia questions?

Jen & Tim Show: What TV show is SO good, you've watched it more than once?

Trump Toohey: Which actor played Bob Dylan in his 2024 biopic 'A Complete Unknown'?

Jen & Tim Show: Summerween, Labubu's and Stolen Flamingos

A 3rd grade teacher played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What is the name of the cell phone company co-owned by Ryan Reynolds?

Trump Toohey: For which 2013 drama film did Matthew McConaughey win the Academy Award for Best Actor?

Trump Toohey: Which Taylor Swift album does the song ‘Look What You Made Me Do’ appear on?

Jen & Tim Show: From Valet to Bidet

Trump Toohey: Jessie J teamed up with Ariana Grande and Nicki Minaj for which song?

Jen & Tim Show: RIP Slider Dave

Trump Toohey: Which animated film series features Miranda Cosgrove as the voice of Margo?

Jen & Tim Show: Goodbye IX-Center?

Jen & Tim Show: The Tales of Slider Dave and Jungle Nate

Jen & Tim Show: The Foot Follow Up

Trump Toohey: Which major league baseball team plays at Fenway Park?

Jen & Tim Show: Tim has two left feet

Jen & Tim Show: Jen is the Pickle Princess

Trump Toohey: What is the name of Batman’s secret hideout?

Jen & Tim Show: Sprite forward with a tea finish

Today's contestant during 'Cleveland, How Much Do You Make?' is a Department Manager for Patient Access

Trump Toohey: Duck Dynasty aired from 2012-2017 on which network?

What is the name of the friendly dinosaur in The Wiggles?

Jen & Tim Show: Bigger the purchase, bigger the screen

A Warehouse Supervisor played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What is the name of the green Squishmallow with a mustache that likes to draw?

Jen & Tim Show: Back to back to back to back to back

Trump Toohey: What type of establishment is Cheers?

Today's contestant during 'Cleveland, How Much Do You Make?' owns a bounce house company

Jen & Tim Show: From Hallway to Mouth

Trump Toohey: What is the name of the show that Ariana Grande’s character Cat later appears in after Victorious ends?

Jen & Tim Show: From a Midge Mess to a Midge Schmear

Trump Toohey: Which Shark Tank product is considered the most successful, earning over $500 million in revenue?

Trump Toohey: What’s the minimum number of seats a theater must have to be considered a Broadway theater?

Jen & Tim Show: Who is most likely to…

A Practice Manager and Patient Advocate played a round of ‘Cleveland, How Much Do You Make?’

Trump Toohey: What is the real name of the Bachelor Mansion?

Jen & Tim Show: The Case of the Black Finger

Trump Toohey: What was the title of the Breaking Bad spinoff show, starring Bob Odenkirk, that ran for 6 seasons?

Jen & Tim Show: Soggy Bottom

Today's contestant during 'Cleveland, How Much Do You Make?' works in shipping and receiving at a warehouse

Trump Toohey: What is the name of the Bravo reality series that follows a group of young people who work aboard yachts?

Jen & Tim Show: Do you have a phonebrella?

Trump Toohey: What iconic luxury fashion brand has Harry Styles frequently collaborated with?

Jen & Tim Show: Mama Month

Trump Toohey: Who is the musical cat that loves to sing and play instruments in the show Gabby’s Dollhouse?

Today's contestant during 'Cleveland, How Much Do You Make?' works in a lab developing colors for cars

Trump Toohey: What was the very first location in the Real Housewives franchise?

Trump Toohey: On the show Love Island, what is the name of the twist where new Islanders enter mid-season?

Jen & Tim Show: A thin fabric to your skin

A Middle School Teacher played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Sydney Sweeney and MGK have known each other since starring in which 2021 musical/romance?

Jen & Tim Show: Tim is looking swole

Trump Toohey: It's square root day! What is the square root of 36?

Jen & Tim Show: Tim did NOT listen to the dress code!

Trump Toohey: What actor plays the main role in the Mission: Impossible series?

Jen & Tim Show: Acceptable Mother's Day Gifts and Top Thrill 2

A Service Manager played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: John Cusack starred opposite Kate Beckinsale in which 2001 romantic film?

Trump Toohey: Martin Short is on which HULU show starring Steve Martin and Selena Gomez?

Trump Toohey: Blake Lively has a new movie coming out this weekend, also starring Anna Kendrick. What’s the name of that film?

A Logistics Manager played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What is the name of the beer released by Great Lakes Brewing every year just before Christmas?

How well do you know the Jen and Tim Show?

Trump Toohey: The band HAIM consists of how many sisters?

Jen & Tim Show: Meet us at The Feve

A Technical Recruiter played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What is the name of the school that Wednesday Adams attends?

Trump Toohey: What Ivy League university did John Mulaney graduate from?

Trump Toohey: What is the name of Olivia Rodrigo’s debut album?

Jen & Tim Show: AI Action Figure Fail

Trump Toohey: What does the “B” in Michael B. Jordan stand for?

Jen & Tim Show: Are you dyeing Easter eggs this year?

Trump Toohey: What kind of Jeep does Cher drive in Clueless?

Jen & Tim Show: The Flamingo is Back!

Trump Toohey: What instrument does Lisa Simpson play?

Jen & Tim Show: Producer Stevie might go to tax jail

Trump Toohey: Anna Kendrick played the role of Beca in which 2012 comedy?

A Graduate Medical Education Administrator played a round of 'Cleveland, How Much Do You Make?'

Jen & Tim Show: You need a hooter

Trump Toohey: On what day of the week does the detention take place in the film 'The Breakfast Club'?

Jen & Tim Show: Hear That Hoot

Trump Toohey: Which pop icon famously wore a green Versace dress to the 2000 Grammy Awards?

Jen & Tim Show: From Feet to Meat

Trump Toohey: What is the name of the town Bella moves to in Twilight?

Jen & Tim Show: Cheek Shaker

Trump Toohey: What is the name of Gordon Ramsay's signature beef dish?

Jen & Tim Show: Dump Dat

An Elementary School Music Teacher played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Which team did the Ohio State Buckeyes football team defeat to win the National Championship this year?

Jen & Tim Show: Does Producer Stevie Know the Nominee?

Trump Toohey: What is the default player character’s name in Minecraft?

Jen & Tim Show: Sorry, your package has been mis-shipped

Trump Toohey: What is the name of Phineas and Ferb's pet platypus?

Jen & Tim Show: Petty revenge suggestions

A Systems Support Analyst played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What power up allows Mario to fly in Super Mario Bros 3?

Jen & Tim Show: What did you realized WAY too late in life?

Trump Toohey: Which film earned Jennifer Lawrence her first Academy Award for Best Actress?

Joey McIntyre revealed his one critique of the 'Wicked' movie and shared what to expect from his solo tour

Jen & Tim Show: We got a winner for Dead Guy In An Envelope! April Fools…

A Retail Manager played a round of 'Cleveland, How Much Do You Make?'

Trump Toohey: What does HBO stand for?

Jen & Tim Show: The Tim Chill Out and Breadcrumbing

Trump Toohey: What is the name of the main protagonist in The Legend of Zelda series?

Jen & Tim Show: Have you ever gone corning or forking?

Trump Toohey: Which Paul brother boxed Mike Tyson just months ago?

Jen & Tim Show: The clipboard people are back and more intense than ever

A Medical Assistant Played a Round of ‘Cleveland, How Much Do You Make?’

Trump Toohey: What is the in game currency used in Fortnite?

Jen & Tim Show: What did Producer Stevie hide from her dentist?

Trump Toohey: What is the name of Snoopy’s western-hat wearing brother from a desert town near Arizona?

A 'Habilitation Coordinator' Played a Round of 'Cleveland, How Much Do You Make?'

Trump Toohey: Name any other sauce you could get at Chick Fil A aside from their signature sauce

Jen & Tim Show: Crappie Fish and Laundry Hacks

Trump Toohey: Which DQ treat is a union of hot fudge and peanuts paired with their world-famous soft serve?