Monahan began his musical career singing with cover band Rogues Gallery from 1988 to 1990. The band consisted of Monahan (lead vocals, percussion), Mark Emhoff (lead guitar, vocals), Mike Imboden (bass, keyboards, vocals), John McElhenny (drums, vocals) and his brother Matt McElhenny (rhythm guitar, keyboards and vocals), in his hometown of Erie, Pennsylvania. After the dissolution of the band, he left Erie in late 1993 and moved to California, where he met Rob Hotchkiss. While progressing from the SF coffeehouse circuit to the LA club scene, Monahan and Hotchkiss added Jimmy Stafford (guitar), Charlie Colin (bass), and Scott Underwood (drums) to their lineup, thus officially forming Train. From 1994 to 2006, Monahan released four studio albums with Train. In 2002, the band earned two Grammys, one of them for the song "Drops of Jupiter (Tell Me)", which was written by Monahan and inspired by his late mother, who had died of cancer.
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