Widely considered one of the most talented actors of his generation, Benicio Del Toro has created an impressive resume of film work, playing an eclectic array of characters throughout his 27-year career. The Academy Award-winner returns to the big screen on September 25 as a hit man in the new crime thriller ‘Sicario.’ So here’s a look back at his remarkable career.

Big Top Pee-wee (1988)

It’s hard to believe now, but the future Oscar winner began his career playing Duke the Dog-Faced Boy in ‘Big Top Pee-wee.’ While it was a small role, it did give Del Toro a chance to appear in his first high-profile summer sequel.

License to Kill (1989)

The actor’s second on-screen role was as a Bond villain in ‘License to Kill,’ which was the final film in the franchise starring Timothy Dalton. Del Toro played Dario, one of evil-mastermind Franz Sanchez’s (Robert Davi) henchmen.

Swimming with Sharks (1994)

Another small role early in Del Toro’s career was Rex, the former assistant to insane movie mogul Buddy Ackerman (Kevin Spacey) in ‘Swimming with Sharks.’ Released at the height of the ‘90s independent film movement, the movie was ahead of its time and exposed the “real Hollywood” long before ‘Entourage’ ever existed.

The Usual Suspects (1995)

Del Toro’s ‘Sharks’ costar Kevin Spacey actually recommended him to director Bryan Singer for ‘The Usual Suspects.’ The actor played incoherent criminal Fred Fenster, a fan-favorite role that made Benicio Del Toro a household name.

Fear and Loathing in Las Vegas (1998)

For his role as Dr. Gonzo in ‘Fear and Loathing in Las Vegas,’ Del Toro gained more than 45 pounds in nine weeks. The film, which was based on Hunter S. Thompson’s seminal novel of the same name, has gone on to become a cult classic.

Traffic (2000)

Del Toro won an Academy Award for Best Supporting Actor playing Mexican police officer-turned-DEA operative Javier Rodriguez in director Steven Soderbergh’s critically acclaimed film ‘Traffic.’ The Oscar win cemented Del Toro as one Hollywood’s finest actors, and his performance in ‘Traffic’ is still considered the best of his career.

The Way of the Gun (2000)

In 2000, the actor reunited with ‘Usual Suspects’ screenwriter Christopher McQuarrie for the director’s debut, ‘The Way of the Gun.’ Since its initial release, the film has reached cult status for its intense level of violence and unexpected plot twists.

Snatch (2000)

Del Toro next appeared in director Guy Ritchie’s ‘Snatch,’ in the minor but memorable role of Franky Four Fingers, a jewel robber and gambling addict. Similar to his role in ‘Usual Suspects,’ Del Toro used the opportunity to create another eccentric but lovable character.

Sin City (2005)

The Oscar winner made his first appearance in a film based on a comic book when he played Det. Lt. Jack “Jackie Boy” Rafferty in directors Frank Miller and Robert Rodriguez’s ‘Sin City.’ In another minor role in a high-profile film, Del Toro proved that in addition to being an excellent leading man, he is also one of the finest supporting actors in the business.

The Wolfman (2010)

Fulfilling a childhood dream, Del Toro played Laurence Talbot in ‘The Wolfman,’ the 2010 remake of the classic 1941 monster movie of the same name. Working with legendary makeup artist Rick Baker, the actor insisted on using practical effects instead of CGI for his Wolfman look. The movie failed at the box office, but it did have its fans.

Savages (2012)

In one of his best performances since ‘Traffic,’ the actor played psychopathic Mexican cartel enforcer Miguel “Lado” Arroyo in director Oliver Stone’s ‘Savages.’ While there are very few similarities between Arroyo and Del Toro’s role as Javier Rodriguez in ‘Traffic,’ it is ironic that both characters end their respective movies by watching children playing baseball.

Guardians of the Galaxy (2014)

After his cameo in ‘Thor: The Dark World,’ Del Toro reprised his role as Taneleer “The Collector” Tivan in director James Gunn’s Marvel Comics-based movie ‘Guardians of the Galaxy.’ Unfortunately, fans had to sit through all of the credits in order to see the actor’s best scene in which he trades insults with Howard the Duck.

Inherent Vice (2014)

In yet another small but memorable role, Del Toro played Sauncho Smilax in director Paul Thomas Anderson’s ‘Inherent Vice.’ As the attorney to Larry “Doc” Sportella (Joaquin Phoenix), Smilax appeared only a few times, but Del Toro’s performance was nonetheless unforgettable. 

Escobar: Paradise Lost (2015)

The actor’s most recent on-screen appearance was as real-life Colombian drug lord Pablo Escobar in ‘Escobar: Paradise Lost.’ Opposite Josh Hutcherson as a young Canadian surfer that falls in love with Escobar’s niece, Del Toro is both equally engaging and menacing at the same time.