Josh Groban will be playing Andy Bernard’s brother on the upcoming season of NBC’s The Office. 

The singer is no stranger to bit acting parts, having appeared as himself, and other characters in both television shows and movies over the years. Earlier this year he even performed a singing rendition of Kanye West’s tweets on Jimmy Kimmel Live!

Here are his 5 best cameos. 

1) Ally McBeal. Show creator David E. Kelly created the character Malcolm Wyatt for the show’s season finale in 2001. Groban played a graduating senior who wowed the cast with a performance his real-life song “You’re Still You.”

2) Glee. The singer has appeared twice — as a slimey version himself — on Fox’s singing show. In the first season’s “Acafellas” episode, he delivered the glee club’s former director Sandy Ryerson (Stephen Tobolowsky) a restraining order. In his second appearance, he served as a judge at the glee club’s regionals competition on the season finale. 

3) American Dad! In the Fox animation show Groban tried his hand at voice overs, playing a whiny parishioner in 2005. Molly Shannon and Marley Shelton also lent their voices to characters in the episode. 

4) Robot Chicken. Clearly a fan of animation, he voiced the video-game character Bill in the Adult Swim show’s fifth season episode “Catch Me if You Kangaroo.”

5) Crazy Stupid Love. Groban made the jump to the big screen in this summer’s RomCom Crazy, Stupid, Love starring Steve Carrell and Ryan Gosling. The singer played Richard, Emma Stone’s lawyer boyfriend who couldn’t commit.