Black appeared in an un-aired pilot episode for a show directed by Ben Stiller and written by Dan Harmon and Rob Schrab called Heat Vision and Jack where he played an ex-astronaut pursued by actor Ron Silver. He was accompanied by his friend who had merged with a motorcycle, voiced by Owen Wilson. This pilot led to his friendship with Harmon and Schrab that resulted in him making many cameos for Channel 101.
In 2000, Black appeared in High Fidelity as a wild employee in John Cusack's record store, a role which Black himself considered his breakout, the film also reunited him with Tim Robbins, who had appeared with Cusack and Black in Bob Roberts eight years earlier. His career soon led to leading roles in films such as Shallow Hal, Orange County, School of Rock, Envy, Shark Tale, King Kong (2005), Nacho Libre, Tenacious D in The Pick of Destiny, Be Kind Rewind, Kung Fu Panda, and Tropic Thunder. (Oh, and two video games)
Prior to his becoming known for his comedies, a lot of his early acting career involved bit parts in serious movies (he played a crazed assassin in Bob Roberts, the brother of Sean Penn's death row inmate in Dead Man Walking, and in Enemy of the State he played one of the NSA tech-support agents, to name three examples). King Kong (2005) can be considered his first serious role as a star, though he mellowed down his comedic persona a bit in The Holiday and Margot At The Wedding.
In 2009, he starred pretty much As Himself in Tim Schafer's Brütal Legend (only, like, six feet taller), alongside Kyle Gass, Ozzy Osbourne, Lemmy Kilmister, and Rob Halford. This meeting also started allowed him to start a friendship with Schafer, nailing him a minor role in Double Fine's next big game, Broken Age.
Unfortunately, as the turn of the 2010s approached, Black's career began to go down the wrong track. After a praised role in Tropic Thunder, he got cast alongside Michael Cera in the prehistoric comedy Year One, which tanked considerably at the box office and was destroyed by critics. Worse still, it finally revealed his Typecasting habit he did in previous films, resulting in the upset of many audiences. The final star destroying blow, however, came with the massive domestic flop of a film adaptation of Gulliver's Travels, which dealt an even bigger blow to his career. His subsequent filmography had been a string of flops (with the exception of Kung Fu Panda 2 and The Muppets, in which he played a key cameo appearance). Bernie seemed to be a Career Resurrection for him, but despite winning critical acclaim, it never got to a wide release. Fortunately, it seems as though the good notices of the D's album, Rize of the Fenix, managed to keep Black from going completely under, and his next major film after Bernie, the film adaptation of Goosebumps, was well-received by critics and moviegoers and was moderate box office success, sparking some hope that his acting career could be headed back up the ladder. Indeed, Black's next live-action film, Jumanji: Welcome to the Jungle, was an acclaimed box-office smash, and Black himself received praise for pulling off a Gender Bender performance that didn't reduce the character to a joke (despite being comic relief). He is also set to star in The House With a Clock in Its Walls, an adaptation of the book of the same name alongside Cate Blanchett and Kyle MacLachlan.
Black's comedic style combines many key elements from both sides of the traditional double act. Black typically begins a skit in which he presents an earnest introduction to a premise or subject that quickly reveals itself to be flawed or fundamentally ludicrous. Black then switches completely to a far-extreme caricature of human emotion. His would-be straight-man Gass often functions to trigger these outbursts. When appearing in a movie that turns out to be a flop, he even manages to make it bearable through his appearances alone—his role as the villainous bully in The Neverending Story III was claimed by many to be the only good thing about it.
- Creator's Favorite: Commented that his favorite role out of everything he's done is voicing Po in the Kung Fu Panda films.
- Old Shame: He's often expressed regret for getting paid as much as he did for Shallow Hal, a role he was entirely dissatisfied with.
- Retroactive Recognition: Appeared with Sarah Jessica Parker and fellow future star Natalie Portman in the criminally underrated Mars Attacks!.