Tobey Maguire

Sam Raimi cast him as Spider-Man in 2002 when nobody was quite sure he was the right fit for an action hero. The film's opening weekend hit $114 million, a box-office record at the time, and settled the debate. Before that, Maguire spent the years before Spider-Man in prestige indie films (Pleasantville, The Cider House Rules, Wonder Boys), playing nervous, sensitive young men. The superhero franchise gave him something the indie circuit never would have: a household name.

Spider-Man: No Way Home (2021) grossed $1.9 billion and was the first pandemic-era film to break a billion at the box office. Maguire's return was a significant part of the draw, even if he was technically a supporting player in someone else's franchise. The project reinvigorated his interest in acting, after a long stretch where he made barely any films. He's reportedly set to appear in Avengers: Doomsday, which means the Marvel machine isn't done with him yet.

He asked a woman to bark like a seal in exchange for $1,000. She refused. That woman was Molly Bloom, who later wrote the book that became Molly's Game. In the mid-to-late 2000s, Maguire organized high-stakes private poker games in Los Angeles that reportedly netted him somewhere in the $30-40 million range over a few years. In 2011, he settled a lawsuit for $80,000 over winnings from a convicted fraudster. He's a vegan who made poker guests wear Crocs.