Tom Holland has already checked off the kind of career goals most actors spend decades chasing. He landed Spider-Man, led a billion-dollar movie and worked with great filmmakers, including Christopher Nolan on The Odyssey. Still, there is one trophy missing from the shelf, and Holland has not pretended to be indifferent if an Oscar eventually joins the collection. That puts him in similar territory to Timothée Chalamet, who has spoken openly about wanting to become one of the greats. Yet, when Holland discussed his own awards ambitions, he compared himself to Leonardo DiCaprio.
Holland took part in an Esquire UK profile ahead of his jam-packed 2026 movie schedule. During the chat, he looked beyond his contemporaries and pointed to DiCaprio as the career model who makes waiting feel worthwhile. According to the outlet’s feature, Holland set himself a 15-year goal of winning an Academy Award amid a 2017 interview. With six years remaining, the actor said he is still interested but is not choosing every project for its awards potential. He explained:
I think there’s something quite poetic about him winning it later in his career ‘cause I’m sure that felt so special to him. So I’m in no rush, but there is still obviously ambition and desire to one day stand up there and thank my mum.
It is a far more relaxed approach than the one Chalamet has taken publicly. After winning the 2025 SAG Award for A Complete Unknown, the Dune: Part Three star said he was “really in pursuit of greatness,” a line that stood out because actors usually sand down that kind of ambition during awards season. Chalamet later admitted he was disappointed when Adrien Brody won the Oscar instead.
The pursuit continued with Marty Supreme. Chalamet earned another Best Actor nomination at the 2026 Academy Awards, but Michael B. Jordan took home the trophy for Sinners. Chalamet remains Oscarless, though he has already collected three acting nominations and another nomination as one of Marty Supreme’s producers. Holland has not entered that part of the race yet, but his willingness to say he wants the same prize carries some of Chalamet’s refreshing refusal to act above it.
Holland also has several projects that could move him closer. His role as Telemachus in Nolan’s The Odyssey, (which he initially thought he was doing terribly), gives him a major dramatic showcase. Also, the long-in-development Fred Astaire biopic looks like the clearest awards vehicle of his career. The Spider-Man: Brand New Day star began as a dancer in Billy Elliot the Musical, making Astaire a natural fit even before the usual biopic and Oscar calculations come into play.
DiCaprio offers the Uncharted star a useful “measuring stick” that a long wait does not mean a failed career. He received his first nomination for What’s Eating Gilbert Grape in 1994, then spent more than two decades collecting acclaimed performances and near misses before finally winning for The Revenant in 2016.
Holland may admire that patience, but his closest present-day comparison is still Chalamet. Both became franchise stars at a young age and have pursued more demanding work, and neither is shy about seeking the industry’s top acting prize. The difference is that Chalamet is already deep into the campaign, while Holland sounds pretty content to let the right role find him before he starts writing that speech to his mum.
Tom Holland has one heck of a summer with The Odyssey hitting theaters on July 17 and then his fourth leading role as everyones favorite Web Head in Spider-Man: Brand New Day on July 31.