Beginning each performance with their trademark greeting, "Mighty fine and a great big Western 'Howdy,' all you buckaroos and buckarettes," Riders in the Sky simultaneously paid tribute to and poked gentle fun at the classic cowboy songs of the 1930s and '40s, particularly the work of the Sons of the Pioneers, Roy Rogers, and Gene Autry. During the '80s and '90s, the group was notable for its ability to attract fans both firmly within the country tradition (the Riders are members of the Grand Ole Opry) and outside of it. Riders in the Sky are made up of lead singer Ranger Doug (born Douglas B. Green), Woody Paul (born Paul Chrisman) on fiddle and vocals, Too Slim (string bass and guitar), and since the mid-'90s, "Cowpolka King" Joey Miskulin on accordion.

Before forming the band, the Michigan-born Ranger Doug was a member of Bill Monroe's Bluegrass Boys and was also a country music journalist, working at the Country Music Foundation Press as editor of The Journal of Country Music. Prior to joining the Riders, Woody Paul, a formidable swing fiddler, played with Loggins & Messina, and Too Slim was a member of Dickey Lee's band in addition to being a songwriter. The trio formed in the mid-'70s, playing a weekly gig at a Nashville nightclub that led to a slot on Tumbleweed Theater on cable television's Nashville Network (TNN).

Riders in the Sky made their recording debut in 1979 on the Rounder label with Three on the Trail, which set the pattern for their mix of classic and newly composed sentimental western numbers, parodies (like "The Legend of Palindrome," in which a figure resembling television's Paladin is described exclusively in sentences that read the same backwards and forwards), crack swing instrumental work, and Sons of the Pioneers-style harmony singing. They released five albums on MCA in the 1980s, and in 1985 they appeared in Sweet Dreams, the film biography of Patsy Cline. The group returned briefly to MCA in 1987, releasing Riders Radio Theater a year later. The success of that album led to the program Riders Radio Theater on National Public Radio, where the group was already well known from performances on Garrison Keillor's Prairie Home Companion program.

In 1991 the Riders moved to CBS for the children's album Harmony Ranch, which led to a short-lived CBS-TV Saturday morning television show. Riders in the Sky moved to the roots-oriented independent Rounder in 1995 and over the next four years, they released six albums for the label, beginning with 1995's Always Drink Upstream from the Herd and ending with 1999's Christmas the Cowboy Way. In 1999, Riders in the Sky were featured in the Disney/Pixar animated blockbuster Toy Story 2 and this opened up one of their greatest periods of popularity, partially due to how it strengthened their presence in childrens' music. Woody's Roundup: A Rootin' Tootin' Collection of Woody's Favorite Songs, a tie-in to Toy Story 2, appeared in 2000; two years later, the similar Monsters, Inc. Scream Factory Favorites showed up. Meanwhile, the band bounced between indie labels and self-releases -- A Pair of Kings, released on Oh Boy in 2002, showcased the increasingly impressive instrumental talents of Miskulin and Paul; Acoustic Disc's 2003 set Silver Jubilee celebrated the band's 25th anniversary, an event also commemorated with the publication of Don Cusic's book, It's the Cowboy Way! The Amazing True Adventures of Riders in the Sky.

Riders in the Sky remained an unfailing, family-friendly concert draw: their shows featured such novelties as rope tricks in addition to music and humor. Recordings arrived steadily, but these were always on indies, such as the band's own Riders Radio Records, along with Cracker Barrel. Additionally, Ranger Doug hosted a show on SiriusXM Satellite Radio called "Ranger Doug's Classic Cowboy Corral," another sign of how enduring the cowboy ways of Riders in the Sky were. ~ Sandra Brennan & James Manheim, Rovi