October 1, 2025
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,…
Podcast: 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.
October 25, 2023
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…
January 7, 2022
Losing It Over Leo, Episode 18: Don’t Look Up
In the eighteenth episode of Classic Movies Live!’s most popular spinoff, Pierre and Jeff talk about what Leo has been up to since Once Upon a Time in Hollywood, the legacy of Adam McKay, and of course, climate change.
February 13, 2021
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!
January 16, 2021
Losing It Over Leo, Episode 16: 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.
January 9, 2021
Losing It Over Leo, Episode 15: The Wolf of 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.
January 2, 2021
Losing It Over Leo, Episode 14: 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…).
December 26, 2020
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…
December 19, 2020
Losing It Over Leo, Episode 12: J. Edgar
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!
December 12, 2020
Losing It Over Leo, Episode 11: 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!
December 5, 2020
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.
November 28, 2020
Losing It Over Leo, Episode 9: The Departed
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!
November 21, 2020
Losing It Over Leo, Episode 8: The Aviator
In today’s episode, Pierre and Jeff lose it over Leo’s second Scorsese performance!
November 14, 2020
Losing It Over Leo, Episode 7: Gangs of New York
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!
November 7, 2020
Losing It Over Leo, Episode 6: 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.
October 31, 2020
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!
October 24, 2020
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.
October 17, 2020
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!
October 10, 2020
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!
October 3, 2020
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?