[2] Noted for Dulli's grimly acerbic lyrics and influences from soul music, it is considered by critics to be the Afghan Whigs' greatest record,[2] an essential release from the 1990s, and among the best-written breakup albums.

The Afghan Whigs frontman Greg Dulli, an amateur filmmaker during his teenage years, took direct inspiration for Gentlemen's thematic concept from Francis Ford Coppola's 1982 romantic fantasy film One from the Heart, identifying especially with the lead character played by Frederic Forrest.

[4] Having covered Motown songs on the band's final release for the Sub Pop label (1992's Uptown Avondale), Dulli wanted to experiment with more sympathetic sounds through the use of minor keys and slower tempos.

Dulli also drew musical inspiration from Van Morrison's influential 1968 album Astral Weeks, particularly in its use of reoccurring melodic motifs and lyrical images throughout, albeit in different forms.

Despite the band's roots in the Sub Pop label, the critic observed "a decidedly non-grungy brand of guitar rock, with slightly busy drumming and arrangements that mirror the turmoil in Greg Dulli's voice".

[9] In the Los Angeles Times, Richard Cromelin regarded the album as possibly "the most overlooked masterpiece" of 1993 and "a grueling immersion in the latest methods of warfare in the battle of the sexes—a dark, dramatic wallow in lust, shame, guilt, despair, deceit and obsession that's framed in dense, uplifting rock.

"[4] Rolling Stone magazine's Matt Diehl noted "a clean, oddly detached hard-rock sound that shifts erratically between purgative and disarmingly pretty, adding tension to Dulli's caterwauling".

[13] Reviewing Gentlemen in March 1994 for The Village Voice, Robert Christgau applauded the raw recording quality and wrote in conclusion: Those conflicted guitars are a direct function of the singer-writer-producer-guitarist's agonized self-exposure/-examination.

[20] Commenting on its legacy at the time of the reissue, Orlando Weekly writer Ashley Belanger said, "It's heralded as one of the best break-up records ever written and considered an essential '90s release, due to the Whigs' creative fusion of R&B with that post-punk alternative rock sound signature to that era.