He is known for his work as a correspondent on The Daily Show with Jon Stewart (2002–2006) and for his starring role in the film Hot Tub Time Machine.

By his second year, he focused much of his attention on Drama classes and plays including Torch Song Trilogy, Ten Little Indians, Cat on a Hot Tin Roof, Romeo and Juliet, and Reckless.

His early paying jobs included working as a security guard at The Metropolitan Museum of Art[7] and handing out menus for a Mexican restaurant.

On October 4, 2005, his younger brother Nate Corddry made his first appearance as a Daily Show correspondent.

He has also made appearances in Old School (2003, credited as Robert Corddry), Blades of Glory, Semi-Pro, I Now Pronounce You Chuck and Larry, Failure to Launch and The Ten.

He also appeared in Harold & Kumar Escape from Guantanamo Bay as Ron Fox, a neurotic and racist agent with the United States Department of Homeland Security, in W. as Ari Fleischer, and also in What Happens in Vegas.

Corddry has appeared in a Curb Your Enthusiasm episode entitled "The Seder" as a sex offender who moves into Larry David's neighborhood.

Corddry has also done some voice work as Gordon the animated Devil on Cartoon Network's Weighty Decisions (alongside fellow Daily Show correspondent Ed Helms).

[14] Corddry wrote, directed, and starred in the web series Childrens Hospital for The WB on its online network at TheWB.com.

[15] After talks fell through with Comedy Central, Turner's Adult Swim picked up the series and began airing new episodes August 22, 2010.

[16] On March 29, 2010, he was a co-guest host of WWE Raw with fellow cast member Clark Duke from Hot Tub Time Machine.

[17] Corddry played an important role in proliferating Justin Halpern's Twitter account Shit My Dad Says.

[20] On December 3, 2019, it was revealed that Corddry would be a host of the revived Top Gear America, which debuted on Motor Trend in January 2021.