Evolving from a garage punk band in the vein of the Replacements, Dinosaur Jr, and Mudhoney to a literate, pretentious, soul-inflected post-punk quartet, the Afghan Whigs were one of the most critically acclaimed alternative bands of the early '90s. Although the band never broke into the mainstream, they developed a dedicated cult following, primarily because of lead singer/songwriter Greg Dulli's tortured, angst-ridden tales of broken relationships and self-loathing. The Afghan Whigs were one of the few alternative bands around in the late '90s to acknowledge R&B, attempting to create a fusion of soul and post-punk.

The Afghan Whigs were formed when the members — vocalist/rhythm guitarist  Greg Dullii, bassist John Curley, lead guitarist Rick McCollum, and drummer Steve Earle— were attending the University of Cincinnati. Dulli, who was raised in Hamilton, OH, was studying film at the university, where he met fellow students McCollum and Earle. Unlike the rest of the band, Curley didn't attend the University of Cincinnati. He arrived in the city to intern as a photographer at the Cincinnati Enquirer, which his father — who published USA Today — arranged for him; for the next few years, Curley continued to shoot pictures for the paper, quitting only when the band's schedule became too busy for him to work both jobs. Dulli happened to meet Curley when visiting a friend's apartment building. Eventually, the pair formed the Afghan Whigs in 1986, along with McCollum and Earle.

In 1988, the Afghan Whigs released their debut album, Big Top Halloween, on their independent record label, Ultrasuede. The album received good word-of-mouth in underground music publications and college radio. A copy of the record worked its way to the influential Seattle-based independent record label Sub Pop, and the label arranged for the Whigs to release a one-off single. The single led to a full-blown record contract with Sub Pop. Up in itt, their first Sub Pop album, was released in 1990. For the next two years, the Afghan Whigs toured America consistently, occasionally heading over to Europe and England. In 1992, their third album, Congregation, was released to very positive reviews. After its release, the band was courted by a number of major labels. The band released one more record on Sub Pop, an EP of soul and R&B covers called Uptown Avondale, and signed to Elektra Records.

Gentlemen, the band's major-label debut, was released to considerable critical acclaim in the fall of 1993. "Debonair," the first single pulled from the album, received major play from MTV, and all of the reviews were positive. Nevertheless, the band wasn't able to ascend past cult status and all the critical praise even engendered a backlash, most notably in the form of an anti-Whigs fanzine called Fat Greg Dulli. In the summer of 1994, the band released the What Jail is Like EP to coincide with their American tour. Upon the completion of their international tour in the fall of 1994, the band took an extended break. Steve Earle left the band in the spring of 1995; he was replaced by Paul Buchignanii, just before the band entered the studio to record their fifth album. Black Love, their second album for Elektra, was released in the spring of 1996. Again, the album received positive reviews but the band failed to break out of their cult status. 1965, their first effort for new label Columbia, followed two years later. However, with the bandmembers living in different states, it would prove to be their last; in February of 2001, the band called it quits, citing geographical separation.