Pirates in Men's Pants is a musical advertised on the Liberty Tree website. The tagline for the musical is "Prepare for a jolly rogering." It is a parody of the play The Pirates of Penzance. The play may have originated from the Pirates in Men's Pants hotel and casino in Las Venturas. This may also be another one of Rockstar's adult jokes, as the casino's name can be abbreviated as PIMP.
- An advertisement for Pirates in Men's Pants can be seen on the post-board in the Johnson House in Ganton, Los Santos in GTA San Andreas, and along the walls of the Portland Grand Theft Auto: Liberty City Stories subway station.