The Highwaymen is the name of at least two musical groups:

• A circa 1960 "collegiate folk" group, which originated at Wesleyan University and had a number-one hit in 1961 with "Michael Row the Boat Ashore" and another top-20 hit in 1962with "Cottonfields". Members: David Fisher, Steve Trott, Chan Daniels, Steve Butts and Bob Burnett. As of 2004, all but Daniels are still alive. They have played reunion gigs as recently as 2002. 10 albums to date.

• A country supergroup of outlaw country musicians Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson, famous for their song "The Highwayman."