Everyone likes to point directly at Tobey Maguire’s cringe-worthy turn as emo Peter Parker in Spider-Man 3 and say, “That. Whatever that was is what killed his career.” While that’s a fair assessment of that truly awkward performance, it’s not the whole story.
According to Spider-Man director Sam Raimi’s 2013 Vulture interview, Sony was more than willing to give him and Maguire a chance at redemption. It just took Raimi too long to get a script together for Spider-Man 4. That delay, combined with Maguire turning 35 the year production would begin, caused Sony to pivot to what eventually became The Amazing Spider-Man (2012) reboot, starring Andrew Garfield.
By this time, Maguire had already started producing films, and with critical darlings like 25th Hour (2002) and Seabiscuit (2003) as credits, that seemed like a natural move for him. Unfortunately, his follow-up producing efforts, Rock of Ages (2012), Pawn Sacrifice (2014), and The 5th Wave (2016), all fell way short of earning money. He also suffered a bit of a public image crisis when he was implicated in, and ultimately paid a settlement for his involvement in, an illegal poker club. As of this writing, he’s only got one TV movie in production on his IMDb page, so either he’s decided to focus on family—he is married with two children—or Hollywood has no more interest in anteing up for another Maguire move.