White Boy Rick
For his upcoming part in White Boy Rick, the actor donned a mustache and mullet, acting as a blue-collar factory worker in Detroit.
Angels in the Outfield
The actor hit a home-run with this role, appearing as an LA Angels outfielder in this classic sports film.
Gold
Don't worry - it's just a bald cap! The actor plays an unlucky businessman who finds himself hunting for gold in the jungles of Indonesia.
A Time to Kill
In a more serious role, the actor plays a lawyer faced with an especially polarizing case in a racially divided Mississippi town.
U-571
Showing the actor in yet another dramatic part, the actor starred in this World War II film as a U.S. Navy Lieutenant.
The Wedding Planner
The actor starred as a pediatrician stuck in a love triangle opposite Jennifer Lopez, his wedding planner, in this 2001 romantic comedy.
Fool's Gold
The Wedding Planner would hardly be the last rom-com we'd see this actor in! He'd go on to appear in many others, including acting as a treasure hunter in Fools Gold.
Tropic Thunder
Can't get enough of the tropics? The Fool's Gold leaves the Bahamas for this fictional Vietnam War film from Ben Stiller.
The Lincoln Lawyer
Taking to the courtroom once again, the actor plays a Los Angeles attorney who picks up a case that spirals out of control.
Contact
Long before he starred in Interstellar, the actor was already making his name as a sci-fi superstar in this film written by Carl Sagan and his wife, Ann Druyan.
Killer Joe
Acting on the other side of the law, McConaughey plays a corrupt cop turned hired hitman in this action-packed crime film.
Magic Mike
This might be the same cowboy hat as Killer Joe, but the character couldn't be more different! In Magic Mike, the actor runs a male strip club in Tampa, Florida.
The Dallas Buyer's Club
In his Academy Award winning performance, the actor played an HIV-positive electrician and rodeo cowboy who fights against the FDA in an effort to find a cure.
The Wolf of Wallstreet
From desperate cowboy to Wall Street tycoon, the actor would appear in The Wolf of Wall Street that same year.
EDtv
Starring alongside Woody Harrelson, McConaughey acts, probably for the first time, as a regular guy, part of a reality series centered on normal people.
Free State of Jones
Playing a poor farmer who deserts the Confederate Army, McConaughey stars in this Civil War film based on true events.
Interstellar
Heading into space once again, Interstellar would go on to be one of the most critically acclaimed films of 2014.
The Dark Tower
The actor didn't stand out a bit dressed in all black while shooting in New York City for his film The Dark Tower.
Dazed and Confused
Alright, alright, alright! The actor had his breakthrough in this 1993 coming-of-age comedy, starring alongside actors like Ben Affleck and Milla Jovovich.
The Texas Chainsaw Massacre: The Next Generation
Just a year later, the actor made the jump from laid back bro to crazed killer. Talk about a transformation!