Jonah Hill — Superbad to Two-Time Oscar Nominee

Jonah Hill transformed from the chubby comedy sidekick in Superbad (2007) to a two-time Oscar nominee. Moneyball (2011) earned a Best Supporting Actor nomination, shocking audiences. Wolf of Wall Street (2013) earned a second. He then directed Mid90s, lost significant weight, and became a fashion icon at Paris Fashion Week. His pivot is cheaper than the average star career change because he avoided extreme physical transformations like Theron's 30-pound gain. Hill's $20 million net worth increase from comedy to drama roles outperforms #7 Charlize Theron's comparable period by 15% in award nominations.