While attending Northwestern, he worked as a substitute teacher at Kilmer Elementary School on the North Side of Chicago, Illinois.

In 2010, Lehr signed on as a supporter of Alley Cat Allies,[2] a non-profit advocacy organization dedicated to transforming communities to protect and improve the lives of cats, joking that “As a feral human, I feel a deep connection with these animals.” Lehr is an alumnus of Mee-Ow, an improv group at Northwestern University.

[3] Lehr is also a co-creator, executive producer and star of the Hulu-original series Quick Draw, which premiered in August 2013.

Before 10 Items, he played Christina Applegate's brother in Jesse during its first season (1998) and also appeared in Friends, in the 1996 episode "The One with the Flashback", as Eric.

In 2015, he was reported to be working on a new show for the cable channel HBO called, The Loop, about a couple who decides to give up the daily grind and sail around the world.