Lookout! Records was founded by Lawrence Livermore and David Hayes (2) in 1987. The label was named after both Livermore's band, the Lookouts, and his fanzine, Lookout Magazine. To this day, Livermore insists that the label name was simply supposed to be "Lookout Records" and not "Lookout! Records". In 1989, Hayes quit the label to form Very Small Records. Livermore was later joined by Christopher Appelgren and Patrick Hynes, who would eventually become partners in the label. By the mid 1990s, Livermore had become disenchanted with the more business-like direction the label was taking, and in 1997, he and Hynes retired, with Appelgren, his wife, Molly Neuman, and Cathy Bauer taking over the label. In 2001, Lookout purchased Panic Button Records from Ben Weasel and John Pierson. The new owners of Lookout shifted the label's focus away from the pop-punk sound that it made famous towards more garage and indie rock bands. Unfortunately, Lookout did not find the same success with its new direction that it had in the past. By the mid 2000s, royalty payments went missing and many of the label's biggest names (Screeching Weasel, Green Day, Operations Ivy, The Queers, Avail, and others) began pulling their back catalogs from the label for reissue elsewhere.
The label stopped releasing new material in 2006 but continued to maintain its back catalog until December 2011. In January 2012, it was announced that Lookout had ceased all operations. In October 2018, Lookout records announced that it was returning, releasing its first new album since 2006; The Lookouting! A Celebration of Lookout Records.