He later enrolled at Oberlin College, initially majoring in geology before shifting his focus to a Bachelor of Arts in film theory and technology, graduating in 1996. Helms developed a passion for performing and storytelling during college, which eventually guided his career path toward acting and comedy. His alma mater, Oberlin, also fostered his love for music. In recognition of his artistic contributions, he received an honorary Doctor of Fine Arts degree from Knox College.

Beginning of Career in Comedy and Voice Work

After earning his degree, Helms started his career in New York City as a performer with various sketch comedy groups while working as a trainee film editor. During this time, he also focused on voice-over work, which opened opportunities, including securing a talent agent. His early voice work included campaigns for companies such as CDnow.com, Lycos, and Burger King.

The Daily Show and Breakthrough Role

Helms joined Comedy Central’s The Daily Show with Jon Stewart as a correspondent in 2002, where his segments—especially "This Week in God"—showcased his comedic timing and sharp wit. He remained with the show until 2006, gaining national visibility.

In 2006, Helms was cast in the NBC mockumentary sitcom The Office, playing the role of Andy Bernard. Initially introduced as a recurring character in the third season, he became a regular cast member by February 2007. His portrayal of the quirky and often insecure Cornell graduate became one of the series’ most memorable performances.