 While on a writers' strike from "Saturday Night Live" following the 1987–88 season, O'Brien put on an improvisational comedy revue in Chicago with fellow "SNL" writers Bob Odenkirk and Robert Smigel called "Happy Happy Good Show".While living in Chicago, O'Brien briefly roomed with Jeff Garlin.In 1989, O'Brien and his fellow "SNL" writers received an Emmy Award for Outstanding Writing in a Comedy or Variety Series.