He played the role of Bumper in the musical films Pitch Perfect and Pitch Perfect 2 and the television series Pitch Perfect: Bumper in Berlin. He had recurring sitcom roles as Andy Bailey in Modern Family and Adam DeMamp in Workaholics. He had roles in the films The Intern, The Final Girls, Mike and Dave Need Wedding Dates, Game Over, Man! and When We First Met. He has voiced characters in films including Ice Age: Collision Course and The Lego Batman Movie, as well as in the animated series Uncle Grandpa, Penn Zero: Part-Time Hero, Vampirina, and Green Eggs and Ham.
Devine was born in Waterloo, Iowa, the son of Dennis and Penny Devine. He was raised in Omaha, Nebraska, and graduated from Millard South High School in 2002. He attended Orange Coast College, along with friend and future co-star Blake Anderson.
In June 1995 when he was 11, Devine was walking his bicycle across a road in Omaha. After he waited for three cement trucks to pass, a fourth truck, previously blocked by opposing traffic, struck him while he was in the street. He went under the first two wheels of the 42-ton truck and slid 500 feet. He was knocked unconscious, suffered acute shock and fell into a coma. He was rushed to intensive care, where he woke up two weeks later. He had broken all the bones in both of his legs, had a collapsed lung, developed multiple infections, and it was unknown whether he would walk again. Over several years, he had 26 surgeries and spent much of his time in a wheelchair. Due to the extent of his injuries, Devine was at very high risk of having to have his legs amputated, and having multiple organ failure. It was discovered that the reason he was not killed was that his bicycle took the full force of the truck. Devine regained full mobility but still has extensive scarring on his legs. He said of the accident, "It was really tough because I had to relearn how to walk, stand up, sit up and everything. The legs were totally mangled. I think that experience helped me realize that anything is possible." To pass the time, he would call into his local radio station and impersonate celebrities to entertain himself and others. Upon returning to school, he experienced bullying, but told jokes as a way to deflect attention away from his injuries. He later said that all of this contributed to how he saw comedy as a way of bringing people together.

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