1. "Pleasantville" (1998)
So Tobey plays David, a '90s teen obsessed with a '50s sitcom called "Pleasantville." He and his sister get zapped into the show's black-and-white world. David relishes the simplicity, but when his sister starts educating the ladies about, ahem, sexual liberation, colors start to appear. The town is torn between those who see the colors as liberating and those who see them as corrupting.
It's a whole metaphorical take on cultural shifts, and Tobey nails it!
2. "Wonder Boys" (2000)
In this quirky comedy-drama, Tobey stars as James Leer, an eccentric, troubled writing prodigy. He crosses paths with his professor Grady (Michael Douglas), who's dealing with his own personal and professional issues.
From stealing a celebrity's jacket to shooting a dog (by accident!), James' actions catalyze a series of chaotic events that make up for an odd yet poignant weekend. Tobey's performance here is endearing and layered.
3. "The Good German" (2006)
How 'bout a little historical noir? Tobey's character, Tully, is a soldier who's embroiled in a post-WWII murder mystery in Berlin. He enlists the help of an American journalist (George Clooney) and ends up dead pretty early in the movie. But don't let that fool you — the guy leaves a lasting impact, and his role is crucial to the unfolding of the whole whodunit.
4. "Seabiscuit" (2003)
Yep, a movie about horse racing, but it's way more than that. Tobey plays Red Pollard, a jockey with a difficult past, who teams up with a half-blind horse, Seabiscuit. Together with the horse's owner and trainer, they beat the odds and give hope to America during the Great Depression.
The race scenes are electrifying, and Tobey shows off his skills as an actor, balancing grit with vulnerability.
5. "The Details" (2011)
This dark comedy is like a suburban nightmare. Tobey plays Jeff, a man whose life spirals out of control after raccoons destroy his backyard. What starts as a mission to exterminate the critters leads to extramarital affairs, blackmail, and even murder.
The movie didn't make a big splash in the box office, but Tobey's quirky performance makes it worth a watch.
6. "Brothers" (2009)
In this gripping drama, Tobey plays Capt. Sam Cahill, a Marine who gets deployed to Afghanistan. Presumed dead, his bad-boy brother Tommy (Jake Gyllenhaal) steps in to help his grieving wife Grace (Natalie Portman) and kids.
Just as things start to get cozy between Tommy and Grace, surprise! Sam returns, but he's mentally scarred from his captivity. He starts to believe that Tommy and Grace had an affair, and things spiral out of control.
7. "Ride with the Devil" (1999)
Set during the American Civil War, Tobey plays Jake Roedel, a young Missourian who joins a group of Southern bushwhackers. Throughout the movie, he confronts his own loyalties and friendships, especially when he befriends a former slave, Holt (Jeffrey Wright). Their friendship poses moral and ethical questions that mirror the complexities of war.
Tobey's portrayal of a young man torn between his roots and what is right brings depth to this historical drama.
8. "Pawn Sacrifice" (2014)
Stepping into the shoes of chess prodigy Bobby Fischer, Tobey navigates us through the turbulent life of this genius. Focused on the 1972 World Chess Championship against Soviet grandmaster Boris Spassky, Tobey shows us Fischer's descent into paranoia. The Cold War setting adds to the intensity, making each chess move feel like a geopolitical battle.
The film does a great job of capturing the tension-filled atmosphere, driven in large part by Tobey's focused performance.
9. "The Ice Storm" (1997)
Taking us back to the '70s, Tobey plays Paul Hood, a teen stuck in a dysfunctional family during Thanksgiving weekend. He has a crush on his neighbor and friend, Libbets (Katie Holmes), and navigates complex familial relationships, including parents who are exploring the swingers' lifestyle. A tragic accident occurs that shocks everyone back to reality.