PODCAST · society
5 Random Questions - Conversations with Creators and Curious Minds
by Danny Brown
What do you get when you ask smart, curious people five completely random questions? You get real stories, weird tangents, and conversations they’ve never had before.On the award-winning 5 Random Questions, host Danny Brown invites creators, entrepreneurs, and fascinating humans to skip the pitches and ditch the talking points - and just show up as themselves.There’s no script. Just five surprising prompts dropped throughout a relaxed, unpredictable conversation. Think laughter, awkward hypotheticals, personal confessions, and the kind of answers that can only come from being caught completely off-guard.Every guest also flips the mic and asks Danny a random question of their own - because fair’s fair.If Hot Ones and WTF with Marc Maron had a podcast baby, this would be it - minus the hot sauce, but with all the spice.New episodes weekly. Always real. Sometimes ridiculous. Never boring.> Winner of the Best Interview Podcast at the 2025 Ear Worthy Podcast Awards> Featured by Apple
Episodes
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Bonus: This Week in Fandom History - Artifacts: Stories from the Emotional History of the Internet
Enjoying the show? Support it here. I recently discovered This Week in Fandom History, a podcast exploring the history of fandom, internet culture and the communities that grow around the things people love. It felt like such a natural fit for the Artifacts audience that I wanted to introduce you...
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Artifacts — Official Trailer - Artifacts: Stories from the Emotional History of the Internet
Remember Winamp skins? Burned CDs? AIM away messages? The Dreamcast? Those weird little corners of the internet that somehow felt more human than everything online today? Maybe we don’t actually miss the technology. Maybe we miss how it made us feel. Artifacts is a podcast about forgotten...
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Jon Powell: Riding an Elephant to the Taco Drive-Thru
This week on 5 Random Questions, podcaster and geeky dad Jon Powell tells us about riding his elephant to the taco drive-thru, what devious prank he'd play on his daughter, how to spend a million dollars, and more. Answering the questions this week: Jonathan Powell Jonathan is the co-host of the...
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Kevin Ryan: Screw the Kids, We're Kidnapping Santa!
This week on 5 Random Questions, podcaster and improv comedian Kevin Ryan expands on why Santa needs to be kidnapped, why his fiancee would go to war with Australia, his beef with elephants, and more. Answering the questions this week: Kevin Ryan Kevin Ryan is the host of the Tyrant In Training...
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Hem Brewster: Bezos, Musk, and the Enshitifcation of Existence
This week on 5 Random Questions, podcaster, producer, and games master Hem Brewster talks about the enshitification of existence, how good-hearted humans can still cause damage to nature, the universal language of swearing, and more. Answering the questions this week: Hem Brewster is a full time...
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That's a Wrap on Season 5, and When to Expect Season 6
Season 5 has officially wrapped, and before I take a short break, I just wanted to jump on the mic and say… thank you. Season 6 will be dropping mid-April, and I can’t wait for you to hear what’s coming next, with more fantastic guests, more unexpected conversations, and plenty more moments where...
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Derick McDuff: When You Imitate The Shining
This week on 5 Random Questions, podcaster and movie buff Derick McDuff talks about the time life almost imitated The Shining, finding an emotional support cat during COVID, why he's a fan of Kobayashi Maru, and more. Answering the questions this week: Derick McDuff Derick McDuff is the host,...
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Rye Voss: Did the CIA Plant Media Operatives?
This week on 5 Random Questions, podcaster and amateur beekeeper Rye Voss talks about letting kids just be children while they can, did the CIA plant media operatives, how two simple words can break a household, why he wants to revisit his 22 year old self, and more. Answering the questions this...
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Austin Grey: Would Zombie Richard Pryor Save the World?
This week on 5 Random Questions, comedian and podcaster Austin Grey talks about bringing back Richard Pryor from the dead to save the world, a burning pretzel for a birthday cake, why irony maybe bypasses Americans, and more. Answering the questions this week: Austin Grey An Austin based comedian...
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5 Random Questions Live - Shape the Events!
I'm looking to run some live recordings of 5 Random Questions starting late spring / early summer, and I'd love for you to help shape where, and what they'd look like. Click the poll link below to share your preferences! 5RQ Live poll Products I Use for 5 Random Questions Note: these may contain...
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Introducing the 5RQ Companion, and Live Recording News
In this bonus episode of 5 Random Questions, host Danny Brown shares details about the 5RQ Companion newsletter, as well as some potential live recording to come for the show. Further reading for this episode The Sixth Question - The 5RQ Companion The 5RQ Companion Products I Use for 5 Random...
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Ewan Spence: Do Zombies Still Go to Work in an Apocalypse?
This week on 5 Random Questions, podcaster and BAFTA nominee Ewan Spence ponders on what zombies actually do in a zombie apocalypse, lessons from Billy Connolly, why kids should be left alone to read, and more. Answering the questions this week: Ewan Spence Ewan is a freelance broadcaster and...
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Matt Cundill: How Do You Accidentally Waste $10 Million?
This week on 5 Random Questions, Matt Cundill shares why he'd be terrible to give $10 million to, live streaming Metallica from the North Pole, how AM shaped his youth, and more. Answering the questions this week: Matt Cundill Matt Cundill is a recovering broadcaster turned podcast producer and...
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Susan Barry: Doesn't Everyone Have Sock Knitting Beans?
In this week’s 5 Random Questions, Danny chats with Susan Barry, host of the award-winning Top Floor podcast and fonder of Hive Marketing. They discuss everything from why pineapple belongs on pizza, beans that can knit socks, the perfect day, and more. Answering the questions this week: Susan...
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Emily Williams: Would You be a Good or Bad Superhero?
In this week’s 5 Random Questions, Danny chats with Emily Williams, a Webby, Signal and Anthem award-winning podcast host, and former Executive Director of the Arcus Center for Social Justice Leadership. They discuss everything from a life-changing loss, cats owning dogs, superhero shenanigans…
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Rob Lynch: What Exactly Is a Good Looking Melon Head?
In this week’s 5 Random Questions, Danny chats with Rob Lynch, author of "Voudon Caliber". They discuss everything from wealth creating toxic people, creativity, why he'd want a melon for a head, and more. Answering the questions this week: Rob Lynch I've always been a jack of all trades, but…
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2025: A Thank You (and What’s Coming in 2026)
2025 was a banner year for 5 Random Questions, and so I wanted to pause and say thank you. In 2025, the show won Best Interview Podcast at the Ear Worthy Podcast Awards, was signed to the Mercury Podcast Network, featured by Apple Podcasts, made the Top 20 Podcasts on Apple, and was even written...
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Keisha "TK" Dutes: Killer Kimonos & Advice That Hurts
Creative conversations rarely go in a straight line. This week on 5 Random Questions, I chat with independent audio producer and educator Keisha “TK” Dutes. We dive into killer kimonos, advice given with good intentions that can still sting, dream homes, and more. Funny, strange, and real - just...
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Deb Brown: Tequila at 3AM with Oliver Stone
On this week's 5 Random Questions, I chat with Deb Brown, author of "From Possibilities to Reality: Save Your Small Town with these Uniquely Do-able Ideas, Projects, and Success Stories". Answers include how she ended up drinking tequila next to Oliver Stone at 3.00am, the secret (and proper) way...
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That's a Wrap on Season 4, and When to Expect Season 5
This season of 5 Random Questions has been a rollercoaster of creativity and fun, and I can't thank you all enough for being part of it. The show took home the prestigious Best Interview Podcast award at the 2025 Ear Worthy Podcast Awards, and that recognition is all thanks to you, the amazing...
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Ana Xavier: Candy Lusting and Busting Stereotypes
On this week's 5 Random Questions, I chat with Ana Xavier, founder of The Podcast Space. Answers include stereotypes and why they need busting, candy from the past and present, making people smile by just being there, and more. Answering the questions this week: Ana Xavier Ana Xavier empowers...
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When the World Feels Heavy, You're Not Alone
This bonus episode is a little different - no guests or random questions, just me sharing a quick reminder that you’re not alone. If life feels heavy right now, or things have been difficult lately, please know that help and support are always available. You matter, and there are people who care…
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Ned Donovan: Failure, Imagination, and Starting Again
On this week's 5 Random Questions, I chat with Ned Donovan - actor, singer, writer, producer, and a bunch of different hyphens around the entertainment industry. Answers include what he really misses about childhood, why failure is success, his favourite day of the year, and more. Answering the...
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My Favourite Podcasts for International Podcast Day 2025
Happy International Podcast Day, everyone! Today, I'm celebrating by flipping the spotlight and sharing some of my favourite podcasts that I think you’ll love too. Think of this as a little podcast tasting menu, where you can sample short trailers from various shows to discover something new to…
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Colin Gray: First Movie Experiences and Tech Disasters
On this week's 5 Random Questions, I chat with Colin Gray, founder of The Podcast Host, and Alitu. Answers include his approach to online movie critics, cartoon memories, tech trip-ups, and more. Answering the questions this week: Colin Gray Colin is a podcaster, speaker, PhD and founder of...
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Jenn Trepeck: Please, No More Inside Out Intestines!
On this week's 5 Random Questions, I chat with Jenn Trepeck, host of the award-winning Salad With a Side of Fries podcast, about hacks for morning routines, wanting to become a teacher to oust a JK teacher, inside out intestines, and more. Answering the questions this week: Jenn Trepeck Jenn...
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Max Kurton: Hamster Dog Things on a Plane
On this week's 5 Random Questions, Max Kurton talks about weird hamster dreams, the parent/child smartness conundrum, teachable tech moments, and more. Answering the questions this week: Max Kurton Max Kurton is an award-winning journalist and content creator with a passion for storytelling in…
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Dan LeFebvre: Best Tips for Time Travellers
On this week's 5 Random Questions, Dan LeFebvre talks about his pet peeves about pet peeves, a time travelling conundrum, the art of not knowing how to describe yourself, and more. Answering the questions this week: Dan LeFebvre Throughout Dan's career, he's produced hundreds of tutorials…
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Charles Commins: How to Plan a 24 Hour Death Party
On this week's 5 Random Questions, Charles Commins shares why old age is a very specific number, death day duties, tetchy tech takedowns, and more. Answering the questions this week: Charles Commins Charles is the host of the award winning It's All Cobblers To Me podcast, founder of podcast...
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5 Random Questions Wins Best Interview Podcast Award
In this short bonus episode, Danny shares the news of 5 Random Questions winning an award in the 2025 Ear Worthy Podcast Awards. Further reading for this episode Announcing The 2025 Ear Worthy Podcast Awards Products I Use for 5 Random Questions Note: these may contain affiliate links, so I get a...
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Colin True: The Trick to Toilet Breaks in Endurance Running
On this week's 5 Random Questions, Colin True talks about his one food for life, his trick to going to the toilet while enduring ultra-running events, a shining moment with his daughter, and much more. Answering the questions this week: Colin True Colin True spent over 20 years working for…
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Martin Gage: What Makes a Great Wonky Wooden Spoon?
On this week's 5 Random Questions, Martin Gage talks about his worst marriage advice, his sojourn into wacky spoons, his begrudged acceptance of board games, and much more. Answering the questions this week: Martin Gage Vice principal, children’s podcast host, author, tractor influencer (big guy...
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Amanda McLoughlin: What Is the Most Useless Superpower?
On this week's 5 Random Questions, Amanda McLoughlin talks about her all-time embarrassing moment, her useless superpower, her perfect last meal, and much more. Answering the questions this week: Amanda McLoughlin Amanda McLoughlin is the CEO of Multitude, a podcast collective, production…
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5 Random Questions Turns One - A Thank You Message
Today, June 27 sees 5 Random Questions turn one, so here's a quick thank you message from me to you. Products I Use for 5 Random Questions Note: these may contain affiliate links, so I get a small percentage of any product you buy when using my link. My equipment: RODE NT1-A large diaphragm...
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That's a Wrap on Season 3, and When to Expect Season 4
That's a wrap on Season 3 of 5 Random Questions, so here's a short, bonus episode to say thank you for becoming a valued listener, and when to expect Season 4. Further reading for this episode Review 5 Random Questions Mercury Podcast Network Products I Use for 5 Random Questions Note: these may...
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Mandy Kaplan: The Embarrassing Night I Bit a Teen
On this week's 5 Random Questions, Mandy Kaplan talks about her need for frequent showers, why she's not afraid to be alone in the house, how she ended up biting a teenager, and much more. Answering the questions this week: Mandy Kaplan Mandy Kaplan is an actress, vo artist, singer, writer…
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Bob LeDrew: What Makes for a Good Alien Ambassador?
On this week's 5 Random Questions, Bob LeDrew talks about why he'd be a great ambassador to welcome aliens, how slapstick shaped his outlook, a teenage event that changed his life, and much more. Answering the questions this week: Bob LeDrew Bob LeDrew is a recovering podcaster... and lots of…
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Evo Terra: What's Better - Haggis or Poutine?
On this week's 5 Random Questions, Evo Terra talks about ska punk, haggis versus poutine, why owning a beer bar isn't bad work, and much more. Answering the questions this week: Evo Terra Evo Terra is an award-winning podcaster and member of the Podcast Hall of Fame. An author of both Podcasting...
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Drew Toynbee: Shower Secrets From a First Date
On this week's 5 Random Questions, Drew Toynbee talks about very personal shower habits, where morals fit when money's on offer, and more. Let's jump in! Answering the questions this week: Drew Toynbee Drew is a freelance digital creative, making fictional and factual video and audio content for...
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Manisha Solomon: Dumb Accomplishments Are the Best
On this week's 5 Random Questions is Manisha Solomon, host & producer of the Archery Parent Podcast. Manisha's topics include what makes her mad at birthdays, why you should celebrate dumb accomplishments, and more. Let's jump in! Answering the questions this week: Manisha Solomon Manisha is an...
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Tom Webster: My Worst Funeral Faux Pas
On this week's 5 Random Questions is Tom Webster, partner at Sounds Profitable and a purveyor of podcasting, stats, and jokes. Tom's topics include funeral faux pas, an Italian love story that also has a future crime in store, why regrets can be the best thing to happen, and more. Let's jump in!...
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Lauren Passell: Why Shower Bellies Are a Great Friendship Test
On this week's 5 Random Questions is Lauren Passell, founder of Tink Media and a hugely popular and respected name in the podcasting space. Lauren's topics include creating a shower belly, why hot sauce isn't just for wings, a water wing childhood that's come full circle in adulthood, and more....
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Tim Truax: Why This Movie Gave Me a Visceral Reaction
On this week's Five Random Questions is Tim Truax, a pop culture podcaster, nerd, and founder of the Canadian podcasting event, PodSummit. Tim's topics include a visceral reaction to a movie scene, why he doesn't like Houston, Texas, how the pandemic ruined his Star Wars moment, and more. Let's...
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Al Grego: Who Says Canadians Don't Complain?
On this week's Five Random Questions is Al Grego, an award-winning podcaster, creator, and producer. Al's topics include wanting to be in a Canadian sitcom, why jump thrills are not for him, his Ted Lasso moment, and more. Let's jump in! Answering the questions this week: Allan Grego Producer and...
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Sean Dillon: How Do You Entertain Elephants?
On this week's Five Random Questions is Sean Dillon, host of the Beyond the Mic podcast. Sean's topics include entertaining elephants, the meaning of hometown, why movies don't really get to him, and more. Let's jump in! Answering the questions this week: Sean Dillon More than 600 episodes of...
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That's a Wrap on Season 2, and When to Expect Season 3
That's a wrap on Season 2 of 5 Random Questions, so here's a short, bonus episode to say thank you for becoming a valued listener, and when to expect Season 3. Further reading for this episode Five Best Independent Podcasts Of 2024 - Ear Worthy Media Products I Use for 5 Random Questions Note:...
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Toronto Mike: My Ultimate Bromance Lineup
On this week's Five Random Questions is Mike Boon, better known as Toronto Mike, the hugely popular podcaster from Canada's biggest city. Mike's topics include the afterlife, why his kids don't get his gum, his favourite bromance, and more. Let's jump in! Answering the questions this week…
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Elsie Escobar: When Being a Mom is No More
On this week's Five Random Questions, Elsie Escobar, podcaster, community builder, advocate, and mentor, talks about missing the mom factor, the origins of excitement, a caffeinated ritual, and more. Let's jump in! Answering the questions this week: Elsie Escobar Elsie Escobar is a transformative...
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Matt Gilhooly: Whiffy Washrooms Have to Go!
On this week's Five Random Questions, Matt Gilhooly, host of The Life Shift podcast as well as author and artist, joins Danny and talks about 30 seconds to change the world, why public bathrooms have to go, why there's no such thing as the perfect fit for people, and more. Let's jump in!…
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Arielle Nissenblatt: The Historical Figure I'd Wedgie
On this week's Five Random Question, Arielle Nissenblatt, a podcast enthusiast and founder of Earbuds Podcast Collective, joins Danny for an engaging chat that includes being tattoo curious, who in history would receive a wedgie, a penile dare, and more. Let's jump in! Answering the questions…
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ABOUT THIS SHOW
What do you get when you ask smart, curious people five completely random questions? You get real stories, weird tangents, and conversations they’ve never had before.On the award-winning 5 Random Questions, host Danny Brown invites creators, entrepreneurs, and fascinating humans to skip the pitches and ditch the talking points - and just show up as themselves.There’s no script. Just five surprising prompts dropped throughout a relaxed, unpredictable conversation. Think laughter, awkward hypotheticals, personal confessions, and the kind of answers that can only come from being caught completely off-guard.Every guest also flips the mic and asks Danny a random question of their own - because fair’s fair.If Hot Ones and WTF with Marc Maron had a podcast baby, this would be it - minus the hot sauce, but with all the spice.New episodes weekly. Always real. Sometimes ridiculous. Never boring.> Winner of the Best Interview Podcast at the 2025 Ear Worthy Podcast Awards> Featured by Apple
HOSTED BY
Danny Brown
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