[10] Encouraged by his parents to pursue music, he started playing the mandolin at an early age, and moved on to the drums, flute, piano and guitar.

After two unsuccessful years, Overstreet started his acting career on the web series Private as Josh Hollis.

[14] Overstreet played the character of Sam Evans, a transfer student and athlete, on the FOX comedy-drama television series Glee.

[17][18][19][20] On April 21, 2011, the video for Hot Chelle Rae's "Tonight Tonight" was released on YouTube and featured a series of cameos of Overstreet alternately making out with a girl (whom he stole from the lead singer) on an office copier, DJing at a club, then playing guitar and mugging for the crowd with his brother, Hot Chelle Rae band member, Nash.

[21] On July 1, 2011, TVLine's Michael Ausiello broke the news that Overstreet's contract option to become a series regular on Glee had not been picked up for season 3, but that he could possibly come back as an occasional guest star.

[22] In reaction to the announcement, fans launched a campaign to promote Overstreet's cover of "Billionaire" and various tags related to the actor, most notably "#DontCutTheChord",[23] began trending on Twitter.

"[27] It was reported on October 18, 2011, and confirmed by series co-creator Ryan Murphy six days later, that Overstreet would be returning to Glee as a recurring character starting with the third season's eighth episode.

[29] Chord has cited James Taylor, David Gray, Jimmy Buffett, Bob Dylan, Paul Simon, and Hall & Oates as musicians that inspire him.

[30] In December 2016, he released a cover of "All I Want for Christmas Is a Real Good Tan", written by Overstreet's father and originally recorded by Kenny Chesney.

[40] Overstreet made appearances as a guest star in a number of television series including The Bold Type,[41] Royalties, and Pickle and Peanut.