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Losing It Over Leo

Having starred in some of the best-performing movies of all time, Leonardo DiCaprio has been widely lauded as one of the best actors of our generation. A teen heart-throb in the 90's, a man's man in the 2000's, and an award-winning A-lister in the 2010s, DiCaprio has delivered award-worthy performances almost non-stop for two decades, and yet the Oscar eluded him until 2016.On this new limited series from the hosts of Classic Movies Live!, Pierre and Jeff go through each period of Leo's career to break down what makes DiCaprio's filmography so special.

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    Losing It Over Leo, Episode 20: One Battle After Another

    It's that time of year again! This week, our hosts are back with the annual episode devoted to the one, the only Leonardo DiCaprio! This time, we're losing it over Leo's first ever collaboration with Paul Thomas Anderson, One Battle After Another! Very loosely based on Thomas Pynchon's novel "Vineland," One Battle stars Leo as Bob Ferguson, an aging revolutionary thrust back into the crosshairs of an anti-immigration anti-domestic-terror general named Steven Lockjaw (Sean Penn). Fifteen years after the dissolution of Bob's revolutionary group, the French 75, Lockjaw finally tracks down him and his daughter, Willa, and decides to wipe out the rest of the group once and for all. One Battle might be PTA's most explicitly political movie -- and one of Leo's -- and couldn't be more of the moment. Despite that, it's far from a cynical political commentary, with just as much to say about what it means to age out of the counterculture. Or even if "aging out" is a viable way to exit the counterculture in the first place. There's a lot to say about Leo's latest, and our hosts are going full spoilers for episode two-zero of Losing It Over Leo!

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    Losing It Over Leo, Episode 19: Killers of the Flower Moon

    Losing It Over Leo is back with another Scorsese picture, and the first movie to feature both Leonardo DiCaprio and Robert DeNiro since This Boy's Life! Killers of the Flower Moon tells the story of the Osage Indian Murders, a series of murders perpetrated against the Osage tribe in Oklahoma during the early 20th century. While Killers features many indigenous people both in front of and behind the camera, the film is nevertheless told by Martin Scorsese, focusing on the non-native perspective. An ideal version of this story would be told by an Osage filmmaker, and we encourage you to seek out indigenous voices in film. You can support indigenous film through organizations like ImagineNative. Be sure to check out Osage reviews of film as well, like this one from Robert Warrior. This episode was produced during the 2023 SAG-AFTRA strikes. Without the labour of the actors currently on strike, the films being discussed in this show wouldn't exist. To learn more about the ongoing strike, go to https://www.sagaftrastrike.org/

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    Classic Movies Live! Podcast Trailer

    The enduring classics of tomorrow, today!

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    Losing It Over Leo, Episode 18: Don’t Look Up

    Just in time for the 94th Academy Awards, Leonardo DiCaprio is back with Don't Look Up! And of course, so is our show Losing It Over Leo! In the eighteenth episode of Classic Movies Live!'s most popular spinoff, Pierre and Jeff talk about what DiCaprio has been up to since Once Upon a Time in Hollywood, the legacy of Adam McKay, and of course, climate change.

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    Losing It Over Leo, Episode 17: Once Upon a Time… In Hollywood

    Since earning his Oscar with The Revenant, Leo has only been in one other movie that's released. That movie is none other than his second collaboration with Quentin Tarantino: Once Upon a Time... In Hollywood! For this 2019 Golden Age of Cinema retrospective, Leo would once again be nominated for an Oscar, alongside co-star Brad Pitt, and director Tarantino. Though he wouldn't win for this one, Once Upon a Time is nonetheless an important coda to DiCaprio's career so far. In this very special epilogue to Losing It Over Leo (so far), our hosts dissect Tarantino's 9th film, and what it says about the careers of those involved. And of course, there's a pretty healthy bit of the episode that deals with Leo's performance, too!

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    Losing It Over Leo, Episode 16: The Revenant

    Well folks, we've finally reached the end of the series. After this episode, Leonardo DiCaprio will finally have gotten his Oscar. That's right, in this episode, we talk about The Revenant. Hot off the heels of Birdman, Alejandro González Iñárritu re-entered Awards Cinema in 2015 with The Revenant, a half-true story about trapper Hugh Glass. A larger-than-life personality even in reality, Glass is given an extra layer of hyperbole by Leo, here giving perhaps his most animated physical performance ever. In addition to Leo, Tom Hardy, Domnhall Gleeson, and Will Poulter join the cast in truly excellent roles. A truly taxin film to make, many of the people involved ended up on hiatus from Hollywood for several years, including Leo, who wouldn't act again until 2019's Once Upon a Time in Hollywood. But most importantly of all, Leo would win an Oscar for his role in The Revenant. Should he have? Our hosts weigh in on this, our final (main) episode of Losing It Over Leo!

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    Losing It Over Leo, Episode 15: The Wolf of Wall Street

    In 2013, Leonardo DiCaprio reunited with Martin Scorsese yet again for a three-hour-long, overtly crude, dark comedy epic about Wall Street. Starring Margot Robbie, Jonah Hill, Matthew McConaughey, and of course Leonardo DiCaprio as Jordan Belfort, The Wolf of Wall Street is a hilarious and occasionally horrifying look at one man's pursuit of the American Dream at the expense of thousands of others. The Wolf of Wall Street would also see Leo earn more Academy Award nominations, this time for Best Picture and Best Actor in a Leading Role. Do our hosts agree that Leo's performance as Belfort was Oscar-worthy? Tune in to find out!

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    Losing It Over Leo, Episode 14: The Great Gatsby

    Back in the 90s, Baz Luhrmann helped launch Leonardo DiCaprio into the spotlight with Romeo + Juliet. While this dynamic duo's work cannot be understated, it would take until 2013 for Luhrmann and Leo to reunite, this time for a sleek, secy re-interpretation of an American classic: The Great Gatsby. Starring Leo in as the exuberantly wealthy titular socialite, Gatsby is an exploration of class, vanity, and the American Dream in the roaring '20s! It also features the reunion of Leo and his good friend Tobey Maguire -- last seen together in the 2001 flop Don's Plum (itself likely the subject of an upcoming episode...). Tune in today to hear our hosts talk about the Great American Party that is the Jay-Z produced F. Scott Fitzgerald movie!

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    Losing It Over Leo, Episode 13: Django Unchained

    In 2012, Leonardo DiCaprio received critical acclaim for a role he took in a movie directed by Quentin Tarantino. But unlike most of his roles, Django Unchained features Leo in an important, but only minor role! For the second episode of our discussion on Late Period Leo, we talk about Quentin Tarantino's first western. Tune in to hear all our thoughts on Leo's most villainous turn, Christoph Waltz's second Oscar win, and Jamie Foxx's epic cowboy hero!

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    Losing It Over Leo, Episode 12: J. Edgar

    Welcome to the most modern period of Leonardo DiCaprio's career. That's right, we've made it to Late Period Leo! And to start this period off, we're talking about Leo's first (and so far only) role in a film by Clint Eastwood. Starring Leo in the title role, J. Edgar tells the story of J. Edgar Hoover, the man responsible for building the FBI into what it is today! But while J. Edgar puts on a tough, no-nonsense persona, he hangs on to secrets that threaten to bring him and the entire bureau down for good! So what did our hosts think about Leo's noir biopic? Tune in to find out!

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    Losing It Over Leo, Episode 11: Inception

    Closing out our discussion of Leo in the early 2000s, this week's movie is Inception! Christopher Nolan's high-concept ensemble action movie about dreams is easily one of the most influential films of this millennium so far! As Inception celebrates its tenth anniversary this year, we discuss Nolan's filmmaking, Hans Zimmer's compositions, Wally Pfister's cinematography, and of course one of Leo's biggest leading roles yet!

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    Losing It Over Leo, Episode 10: Blood Diamond

    In 2006, Leonardo DiCaprio would earn critical acclaim for two back-to-back performances. The first of those was that in year's Best Picture winner, The Departed. The second, Blood Diamond, would net Leo his third-ever Oscar nomination, and second for Best Actor in a Leading Role. Set in Sierra Leone during the civil war in 1999, Blood Diamond stars Leo as diamond smuggler Danny Archer. When Archer meets Solomon Vandy (Djimon Honsou), a fisherman displaced by rebels, the unlikely pair join forces with journalist Maddy Bowen (Jennifer Connoly) to recover a massive pink diamond valuable enough for all three of them to start their lives anew. Part brutal war commentary, part gripping action film, and featuring career-defining performances from all three leads, Blood Diamond was an unlikely, but worthy contender at 2007's Oscars. So what did our hosts think about it? Find out on the tenth episode of Losing It Over Leo!

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    Losing It Over Leo, Episode 9: The Departed

    This week, we present Leo's third collaboration with Martin Scorsese! With The Departed, Scorsese, and an ensemble cast including Leo, Matt Damon, Jack Nicholson, and Academy Award Nominee Mark Wahlberg take on the harsh world of Boston crime. Damon and Leo star as opposing moles in the police force and mob, respectively, locked in an intense battle of wits within a proxy war between Nicholson's ruthless crime boss and Martin Sheen's benevolent police chief. The Departed won Scorsese his first-ever directing Oscar, as well as Best Picture at the 79th Academy Awards. Leo was also nominated for an Oscar at the same ceremony, but notably not for this movie! Was that a mistake? Should this have been the year Leo took home Oscar gold? Tune in and find out on the ninth episode of Losing It Over Leo!

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    Losing It Over Leo, Episode 8: The Aviator

    With What's Eating Gilbert Grape, Leonardo DiCaprio would earn his first Oscar nomination and his only nomination for Best Actor in a Supporting Role. It would be another 20 years before his next nomination, this time for Best Actor in a Leading Role. His second collaboration with Martin Scorsese, The Aviator sees Leo taking on the role of legendary American businessman Howard Hughes. A socially awkward eccentric with a debilitating case of OCD, Hughes is a fascinating character, and one of the most interesting roles Leo has ever played. So what do our hosts think? In today's episode, Pierre and Jeff lose it over Leo's second Scorsese performance!

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    Losing It Over Leo, Episode 7: Gangs of New York

    Leonardo DiCaprio is known for many things, including his frequent partnership with acclaimed film director Martin Scorsese. To date, Leo has starred in 5 Scorsese movies, with more on the way as of 2020. But, as with everything, it had to start somewhere! That somewhere was 2002's Gangs of New York, a $100 million passion project about Irish immigrants in New York City at the time of the American Civil War. Featuring an all-star cast including Leo, Cameron Diaz, John C. Reilly, and Daniel Day-Lewis, Gangs was universally loved by critics, but what did our hosts think of it? Tune in to hear Pierre and Jeff discuss Daniel Day-Lewis, the John C. Reilly Award, Scorsese's career, and of course Leonardo DiCaprio on today's episode of Losing It Over Leo!

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    Losing It Over Leo, Episode 6: Catch Me If You Can

    With Leo's 90's rise to stardom behind them, our hosts turn to Leo's middle period! Between 2000 and 2010, Leonardo DiCaprio starred in some of the best movies of his career, starting with an unforgettable performance in Steven Spielberg's 2003 film Catch Me If You Can! Featuring Leo as legendary scam artist Frank Abagnale, Jr. alongside Tom Hanks as FBI agent Carl Hanratty, Catch Me If You Can sees our illustrious silver screen superman stepping out of the role of teen heartthrob for the first time since Titanic. How does he do outside his comfort zone? What do Pierre and Jeff think of Spielberg's style of historical drama? The answers to these questions and more on this week's episode of Losing It Over Leo!

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    Losing It Over Leo, Episode 5: Titanic

    In 1997, James Cameron released a movie so monumental it would go on not only to be nominated for the most Academy Awards of any movie up to that point (tying 1950's All About Eve) and win the most as well (tying Ben Hur), but also perform so well with audiences it would hold the record for best box office performance for almost 12 years. That movie was the disaster/romance epic Titanic, featuring Kate Winslet, Kathy Bates, Billy Zane, and of course Leonardo DiCaprio! Having now watched Titanic for the first time, Pierre and Jeff talk about the end of an era for Leo, as we close out our discussion of early-period DiCaprio with one of the biggest movies of all time!

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    Losing It Over Leo, Episode 4: Romeo + Juliet

    At the end of the 90's, Leonardo DiCaprio was best known for two movies he made within a year of each other. The first of those movies, starring the young heartthrob in what could be considered his breakout role (if you don't already consider that to have been Gilbert Grape), was Baz Luhrmann's visionary take on William Shakespeare's Romeo + Juliet. Uprooting the story from medieval Italy and transplanting it to 90's California, Romeo + Juliet is a truly bizarre and fascinating recreation of the bard's most well-known romance. And of course, this one stars everybody's favourite actor in the leading role! So what do our hosts think about it? You'll have to listen to find out, but be warned, there's a lot to say! On today's family-sized episode, we discuss Leo's sixth movie! Yes, we skipped a few, and no, you didn't miss an episode!

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    Losing It Over Leo, Episode 3: The Basketball Diaries

    The Basketball Diaries, Leonardo DiCaprio's third movie, and the subject of this week's episode of Losing It Over Leo! Featuring his first onscreen appearance alongside Mark Wahlberg, Basketball sees Leo in the role of teenage drug addict Jim Carroll. As Leo once again dons the persona of a struggling youth, we're left to wonder: how does Basketball stack up against the actors first two movies? Can Leo maintain his so far flawless acting record? Tune in to hear Pierre and Jeff discuss yet another movie from the filmography of one of the greatest living actors!

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    Losing It Over Leo, Episode 2: What’s Eating Gilbert Grape?

    In the second episode of Losing It Over Leo, Jeff and Pierre talk about What's Eating Gilbert Grape. Leo's second movie is also his first Oscar nomination! Tune in to hear our hosts' thoughts on Leo, as well as remarkable early performances from Johnny Depp, Juliette Lewis, John C. Reilly, Mary Steenbergen, and Crispin Glover!

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    Losing It Over Leo, Episode 1: This Boy’s Life

    In the pilot episode of Losing It Over Leo, Pierre and Jeff discuss Leonardo DiCaprio's first movie: This Boy's Life. The only movie to feature both Leonardo DiCaprio and Robert De Niro, This Boy's Life has largely fallen out of the public conscience. That said, is it worth your time? Also, how is the first silver-screen performance from our boy Leo? Tune in to find out!

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ABOUT THIS SHOW

Having starred in some of the best-performing movies of all time, Leonardo DiCaprio has been widely lauded as one of the best actors of our generation. A teen heart-throb in the 90's, a man's man in the 2000's, and an award-winning A-lister in the 2010s, DiCaprio has delivered award-worthy performances almost non-stop for two decades, and yet the Oscar eluded him until 2016.On this new limited series from the hosts of Classic Movies Live!, Pierre and Jeff go through each period of Leo's career to break down what makes DiCaprio's filmography so special.

HOSTED BY

Absolute Trash

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Frequently Asked Questions

How many episodes does Losing It Over Leo have?

Losing It Over Leo currently has 21 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Losing It Over Leo about?

Having starred in some of the best-performing movies of all time, Leonardo DiCaprio has been widely lauded as one of the best actors of our generation. A teen heart-throb in the 90's, a man's man in the 2000's, and an award-winning A-lister in the 2010s, DiCaprio has delivered award-worthy...

How often does Losing It Over Leo release new episodes?

Losing It Over Leo has 21 episodes. Check the episode list to see recent publication dates and frequency.

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You can listen to Losing It Over Leo on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Losing It Over Leo?

Losing It Over Leo is created and hosted by Absolute Trash.
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