With five Academy Award nominations and a win for “The Revenant,” Leonardo DiCaprio has established himself as a Hollywood icon — vaulting from his first starring role in the sci-fi horror “Critters III” to challenging parts with major auteurs, including Quentin Tarantino, Martin Scorsese, Christopher Nolan, and Alejandro G. Iñárritu, while championing humanitarian issues through his prolific environmental activism.

In “Once Upon a Time… in Hollywood,” DiCaprio played a washed-up movie star at the end of his tether, which is perhaps the biggest stretch of the actor’s filmography considering his esteemed pedigree and enviable body of work. With nearly $7 billion dollars of global box office to his name and a list of roles that prove his selective instincts each time out, DiCaprio is one of the few movie stars working today who always delivers something worth seeing.

That even includes Adam McKay’s 2021 end-times satire for Netflix “Don’t Look Up,” which IndieWire’s David Ehrlich gave a “C-” and saw DiCaprio portraying a flustered astronomy professor heralding a planet-annihilating comet to deaf ears. Or take Baz Luhrmann’s blithely mismatched “Great Gatsby” adaptation from 2013: an overly glittery critical misfire that still saw DiCaprio’s majorly depressed fat cat yanking at audiences’ heartstrings opposite Carey Mulligan. Heck, we’d even watch Leo in the titular role of Clint Eastwood’s baffling “J. Edgar” again — if only for the opportunity to stretch our flummoxed lower faces at the 2011 biopic’s jaw-dropping awfulness.

Lesser works aside, DiCaprio is one of Hollywood’s last remaining movie stars and the boys are back in town, with him and Scorsese once again teaming up for a new movie. The buzzy “Killers of the Flower Moon” stars DiCaprio in a more than three-hour Western epic about a string of Oklahoma murders in the Osage Nation from 1921 to 1926; DiCaprio appears with Lily Gladstone, Robert De Niro, Jesse Plemons, Brendan Fraser, and many more. It got a “B+” from IndieWire, and has earned $154 million at the global box office to date. You can read Ehrlich’s complete review here.

To honor the film’s release, and its subsequent march to awards season, IndieWire looks back on DiCaprio’s 20 best performances. Entries are ranked with our condolences to “The Man in the Iron Mask.” Maybe next time, Philippe.

With editorial contributions by Kate Erbland and Jim Hemphill.

[Editor’s note: This article was first published in August 2019 and has since been updated.] 

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