Leonardo DiCaprioandRobert De Niroare among the most iconic actors working today. While both have appeared in their share of critically acclaimed titles, they’ve also collaborated a handful of times, most notablywith Martin Scorsese.Killers of the Flower Moonis the most recent, while DiCaprio and De Niro also appeared in Scorsese’s 2015 short filmThe Audition. But there was another time the two legends shared the screen over 30 years ago.
DiCaprio and De Niro first appeared together in the 1993 dramaThis Boy’s Life, from director Michael Caton-Jones.DiCaprio starred as young Toby Wolff, with De Niro as his mother’s abusive boyfriend. If you’re unfamiliar with this movie, you’re likely not alone,as it seems to live in relative obscurity today. Nowadays, it’s difficult to imagine any DiCaprio-De Niro collab flying so far under the radar. So what went wrong? If you’re thinkingThis Boy’s Lifewas popular at its release and faded away sometime after, that’s also not the case. It reportedly earned just $4 million at the box office on its initial release. No one seemed to care back then, either. So, let’s look at what this movie’s all about and why it was lost to history.
This Boy’s Life Takes an Intimate Look at Abuse
Set in the 1950s, the movie stars Ellen Barkin as Caroline Wolff, the mother of Leo’s Toby. She wants to settle down and find a good man who can provide a better life for her and her son. After moving to Seattle, she meets De Niro’s Dwight Hansen, who seems ideal at first. They marry, and Caroline and Toby move in with Dwight.
The trauma fromCaroline’s separation from Toby’s father causes Toby to begin to act out in school. During this time,Dwight reveals himself as abusive to Tobywhenever Caroline is away. She eventually discovers this but is unwilling to give up on this marriage after things don’t work out with Toby’s father. As the situation intensifies, Toby desires to leave and go live with his father and brother on the East Coast, and he befriends a classmate who’s also experiencing personal struggles.
Toby fakes school records to have a better chance of getting into schools on the East Coast, which strains his relationship with his friend Arthur. He eventually gets into The Hill School in Pennsylvania under a full-ride scholarship. When Dwight learns of this,he physically assaults Toby, forcing Caroline to finally step in and end it. She realizes she doesn’t have to live this way, and she and Toby escape. Toby and Caroline go their separate ways, with Toby off to start a new life at school on the East Coast.
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This Boy’s Lifeseems to check off all the required boxes for its genre.Struggling single mother? Check. Rebellious kid with a troubled home life? Check. A new husband who seems nice but is hiding a dark side? Check. Mother and child joining together to escape the abuse and start a new life? Check. This formula isn’t too daring or revolutionary, but it should have set the movie up for success in the family drama market.
Why This Boy’s Life Didn’t Meet Its Expectations
The movie grossed just $1.5 million over its opening weekend of June 25, 2025, and finished its theatrical run with a domestic total of $4.1 million. These numbers don’t seem to add up, especially when you consider that Robert De Niro and Ellen Barkin were both very much established stars in 1993. Sure, DiCaprio and the rest of the cast were relatively unknown, but wasn’tDe Niro’s top-billed nameenough? The critics seemed to agree, asThis Boy’s Lifesits at an impressive 76% on Rotten Tomatoes.The storyline and cast performances (particularly the young DiCaprio) were all singled out for praise. MaybeThis Boy’s Life’s poor performance wasn’t a result of what it did but rather what it didn’t do.
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Yes, it’s a successful drama, but does it stand out? How often have we seen the “family flees hardship only to wind up with more hardship” trope? It’s not exactly an original angle. That’s not to say that this is a bad thing, but it’s possible that audiences didn’t believeThis Boy’s Lifewould do anything to stand out from the pack.Family dramas are a crowdedfield, and it’s easy for the ones that play it safe to slip under the radar, even if a name like De Niro is attached.
Despite its underperformance,This Boy’s Lifewas a successful launching pad for many of its newer stars. De Niro pitchedDiCaprio to Martin Scorseseafter this film, and Scorsese responded by casting DiCaprio inGangs of New York. This was just the beginning of a lucrative partnership between Scorsese, which would later includeThe Aviator, The Departed, Shutter Island, The Wolf of Wall Street,andKillers of the Flower Moon.
This Boy’s Lifeeven featured the first-ever credited appearance of Spider-Man himself, Tobey Maguire. Chris Cooper, Carla Gugino, and Eliza Dushku made some of their earliest major-label debuts here as well. So, if you’re in the mood for a family drama or just want to see DiCaprio and De Niro’s first onscreen pairing, check this one out.This Boy’s Lifeis available to rent onPrime VideoandApple TV+.
