He is best known for his roles as James "Sawyer" Ford on the ABC television show Lost and as Will Bowman on the USA Network science fiction drama Colony.

[7] Holloway moved to Los Angeles, where he began a successful career as a runway and print model, including for brands Dolce & Gabbana, Calvin Klein and Donna Karan.

[7] In 1993, Holloway appeared in the Aerosmith video for the song "Cryin'" as a thief who tries to steal Alicia Silverstone's backpack from a diner, only to be caught and beaten up by her.

[8] Nevertheless, he found time to star in the thriller Whisper and he also ventured into the world of video games in Command & Conquer 3: Tiberium Wars.

In May 2007, 20th Century Fox approached Holloway for the second time and offered him the role of Gambit in X-Men 4[broken anchor].

Artist Salvador Larroca is believed by Comic Book Resources columnist Timothy Callahan to have used Holloway as the model for his rendition of Tony Stark during his run on Iron Man, which began in 2008.

In 2014, Holloway starred in the lead role in the CBS television show Intelligence as a cybercrime agent who can "access the entire electromagnetic spectrum" with his mind.

[15][16] At the end of shooting the Lost pilot in Oahu, Hawaii, Holloway proposed to his long-time girlfriend, Yessica Kumala.