Sommer kick-started his career with a small role in the 2006 hit The Devil Wears Prada alongside Anne Hathaway, Meryl Streep, and Adrian Grenier. He’s worked steadily in television and film since then and is also a member of the very popular (and talented) Upright Citizens Brigade. As Harry Crane, Sommer is another young man trying to make it in the ever-changing world of advertising. Like Roger, he provides some comic relief, but he’s also been developing the media department of the agency, an increasingly relevant aspect of advertising that makes him an increasingly relevant character in the show.