Jonah Hill — Superbad to Two-Time Oscar Nominee

Hill was the chubby comedy sidekick in Superbad (2007) and Knocked Up. Then Moneyball (2011) earned him a Best Supporting Actor Oscar nomination — shocking everyone. Wolf of Wall Street (2013) earned him a second nomination. He then directed Mid90s (2018), lost significant weight, became a fashion icon (seen front row at Paris Fashion Week in Gucci), and retreated from public life citing mental health. The transformation from Seth Rogen's buddy to double Oscar nominee to fashion-forward introvert is one of the most unexpected character arcs in Hollywood. The comedy sidekick became the main character.