For a band that only released three albums, the Highwaymen have a lot of compilations -- at least four full-fledged CDs prior to this 2016 set, which was released in conjunction with the triple-disc package Live: American Outlaws. The Very Best of the Highwaymen covers familiar ground, adding three selections -- "City of New Orleans," "Big River," and "The King Is Gone (So Are You)" -- from Live: American Outlaws, along with the "One Too Many Mornings" from Johnny Cash and Waylon Jennings' 1986 Heroes, now featuring harmonies by Willie Nelson and Kris Kristofferson. Outside of this, the 16-track collection contains six selections from their first (and best) album from 1985, four tracks from 1990's Highwayman 2 and a couple of cuts from 1995's The Road Goes on Forever. It's a good cross-section of their material and sequenced nicely, making for the best single-disc overview of the supergroup's recordings.
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AllMusic Review by Stephen Thomas Erlewine