After recruiting bassist Jim Sangster to allow frontman McCaughey to switch over to the guitar, the Fellows returned to the studio for 1986's Topsy Turvy, spotlighting the adolescent hijinks of tracks like "You've Got Your Head on Backwards," "Hang Out Right," and "The New John Agar." The following year's The Men Who Loved Music (aka "Chicago 19") and the follow-up Refreshments EP solidified the band's cult following, which included among its ranks a number of other members of the indie music scene; the Replacements' Paul Westerberg considered the Fellows kindred spirits, and the two groups often toured in tandem.

After 1988's Totally Lost, Carroll left the group. In the wake of his departure, the remaining three Young Fresh Fellows issued an authorized bootleg titled Beans and Tolerance (aka "Simply Wonderful, Wonderfully Simple") before enlisting Fastbacks kingpin Kurt Bloch for 1989's rootsy This One's for the Ladies, issued concurrently with McCaughey's solo side project My Chartreuse Opinion.

With producer Butch Vig in tow, the Young Fresh Fellows returned in 1991 with Electric Bird Digest, while Memphis R&B legend Willie Mitchell took over the production reins for 1993's then-swan song It's Low Beat Time. In the wake of the Fellows' demise, McCaughey formed a new band, the Minus 5, an ever-changing aggregate of Seattle area all-stars; additionally, he toured as a sideman with his pals in R.E.M. But the Young Fresh Fellows still had some life to them after all, and a "comeback" album, Because We Hate You, appeared in 2001, followed eight years later by the Robyn Hitchcock-produced I Think This Is from Yep Roc Records. The band's thirteenth long player, Tiempo De Lujo, arrived in 2012.