Basketball Diaries, Onscreen Rehab and Therapy

Island Pictures

Seemingly every hot young actor in Hollywood wanted to star in The Basketball Diaries at some point. 

The decades-long journey to bring Jim Carroll's gut punch of a memoir to the big screen was finally at the casting crossroads, and it was time to fill the role of the former teen basketball talent, hustler and heroin addict who splashed onto the literary scene chronicling his demons and became a celebrated writer, poet, punk rocker and all-around New York cultural icon unto himself.

From Matt Dillon and River Phoenix to Ethan Hawke and Eric Stoltz, the 1980s' freshest faces had all been ready to get dirty at some point over the years. But the years kept going by, and the project kept changing hands.

Leonardo DiCaprio had only made a couple of movies (not including the scenes he shot for Drew Barrymore's femme fatale thriller Poison Ivy that were left on the cutting room floor), but the 20-year-old actor was already Oscar-nominated, for What's Eating Gilbert Grape, and had even already starred in a coming-of-age tale adapted from a memoir, This Boy's Life.

Ultimately, Leo's proven acting chops combined with his physical resemblance to Carroll ("I wasn't quite as thin!" the writer later protested) earned him the part over a slew of his peers. 

"With this role, I saw a character that would take a lot of work and would require a lot of exploration into something I've never dealt with before," DiCaprio told the San Francisco Chronicle in 1995 ahead of the film's April 21 release. "There were a lot of emotions that I would have to deal with, and basically, it was a cool character."

What more could a young star with the world on his plate even pre-Titanic have wanted in a movie?

But of course, much as there are seemingly endless layers of Jim Carroll's life to peel back, there's far more to the story of how The Basketball Diaries was made. And in honor of the film's 25th anniversary, here are the key revelations from that surprising story:

The Basketball Diaries, Jim Carroll

Michael Wolfe

The Basketball Diaries, Leonardo Dicaprio


River Phoenix

George Rose/Getty Images

The Basketball Diaries, Scott Kalvert

Ron Galella, Ltd./Ron Galella Collection via Getty Images

Leonardo DiCaprio, The Basketball Diaries

Metro-Goldwyn-Mayer Studios Inc.

The Basketball Diaries, Mark Wahlberg


The Basketball Diaries, Mark Wahlberg, Leonardo DiCaprio

Ron Galella, Ltd./Ron Galella Collection via Getty Images

The Basketball Diaries, Mark Wahlberg, Leonardo DiCaprio

Frazer Harrison/Getty Images

The Basketball Diaries, James Madio, Mark Wahlberg, Patrick McGaw, Leonardo Dicaprio


The Basketball Diaries, Leonardo DiCaprio, Jim Carroll

Catherine McGann/Getty Images

The Basketball Diaries, Cynthia & Brittany Daniel


The Basketball Diaries, Leonardo Dicaprio, Lorraine Bracco

Moviestore Collection/Shutterstock

Leonardo DiCaprio, The Basketball Diaries

Vivendi Entertainment / New Line Cinema

The film as a whole got mixed reviews and only made $2.4 million, though like any work of art, it has its devoted fans. Both at the time and in hindsight, some critics thought Leo was miscast while others thought he nailed it and emerged a full-blown movie star.

Either way, it was just one of a series of memorable performances for the future Oscar winner.

Talking to Interview magazine in 1994, DiCaprio called playing Carroll "uncharted territory."

"I think actors make the mistake of finding their little niche in the business and once they try to do something a little darker, boom, they get slapped across the face for it, so they go back to what they did before," he explained his relatively short but intense acting CV at the time. "That's why the business can be cruel, because it doesn't encourage you to learn. Like on this movie, there's some whacked-out stuff that I do that I've never done before, never in my entire life, not even at home alone."

The risk-taking paid off.

Carroll observed to the San Francisco Chronicle a later, "You know, I came out of the theater after seeing The Basketball Diaries thinking, 'Leonardo DiCaprio can do anything.'" 

The ensuing years proved him right.

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