16 Biggest Hits Volume II is a 16-track country compilation released in 2007 by Columbia/Legacy, serving as a follow-up to Willie Nelson's multi-platinum original 16 Biggest Hits set. Highlighting his classic late-1970s and 1980s catalog for Columbia Records, this collection gathers essential solo tracks and high-profile collaborations. Key highlights include his timeless duets Pancho & Lefty (with Merle Haggard), Faded Love (with Leon Russell), and Good Hearted Woman (with Waylon Jennings), along with the iconic supergroup anthem Highwayman (with The Highwaymen) and solo favorites like Me And Paul and All Of Me.

Between 1985 and 1995, The Highwaymen recorded three major label albums: two on Columbia Records and one for Liberty. Their Columbia works produced three chart singles, including their number one, signature tune, the Jimmy Webb composition ‘Highwayman’, in 1985. During this time, the members of the group - Willie Nelson, Kris Kristofferson, Johnny Cash, and Waylon Jennings - provided the voice and dramatisation for the Louis L'Amour Collection, a four-CD box set of seven of the author’s stories, published by the HighBridge Company, although the four were not credited as "The Highwaymen" in this work. Besides the four formal members of the group, one other vocal artist appeared on a Highwaymen recording: Johnny Rodriguez, who provided Spanish vocal on ‘Deportee’, a Woody Guthrie composition, from the album Highwayman. The four starred in one movie together: the 1986 film Stagecoach.

Legacy’s 2010 collection The Essential Highwaymen doesn’t merely cover recordings made by the supergroup of Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson, it rounds up selections from their solo albums of the ‘70s, ‘80s, ’90s, and 2000s. Specifically, these selections are written by other members of the group, so the net effect is a generous 36-track collection of Highwaymen highlights in all forms, drawing a more detailed portrait of their crossed paths than any individual album by the supergroup.