[5] He produced or engineered dozens of records including works by prominent artists such as The Jayhawks, The Replacements, Motion City Soundtrack, Soul Asylum, Golden Smog, Dave Davies of The Kinks, Wesley Stace, Mason Jennings, Mark Mallman, John Strohm, Brian Setzer, Lizzo, Pete Yorn, The Wallflowers, Rhett Miller of The Old 97s, Jeremy Messersmith, and Juliana Hatfield.

Though the Dig earned critical praise for the single "Problem With Mary,"[7] Ackerson told an interviewer in 1997 that he felt the band had been too "angry,"[10] and determined to take a more positive tack with his next project.

The third, 1990's Approximately, moved to the larger label Clean (Twin/Tone), but despite the band's increased profile, the album suffered when Twin/Tone's distributor, Rough Trade, went out of business.

Trouser Press writer Ira Robbins praised Approximately as a turning point "for Ackerson, who was on his way to becoming an assured and able multi-faceted rocker.

Bryan Carroll of Allmusic called Fine's blend of shoegazer and Brit-pop "near-perfect" and lamented that "probably due to promotion/distribution, the record never received the praise or audience it deserved.

"[12] After a short stint as second guitarist in Blake Babies singer John Strohm's band Antenna,[13] Ackerson formed Polara with guitarist Jennifer Jurgens, bassist Jason Orris, and Trip Shakespeare's Matt Wilson on drums, continuing his interest in 1960s psychedelic pop but adding a heavy element of Krautrock-inspired electronics and keyboards.

The group released a self-titled debut in 1995, which Allmusic writer Rick Anderson called "weird but lovable" and "as fresh and bracing as a bucket of ice water in the face.

[11] Billboard writer Deborah Russell called Ackerson and Polara the front of "the emergence of a new local (Twin Cities) scene" more interested in pop music and postpunk than the punk rock of bands like Hüsker Dü and the Replacements.

Ackerson took a holistic approach to making music, viewing composition, performance, recording and post-production all as steps in a single process of creating a song.

[20] Despite a generally warm reception by critics (Trouser Press' Ira Robbins called it "stylish and sophisticated"[11]), the album received little support from its record label.

[14] Greg Winter of CMJ called Jetpack Blues "exquisite," with "short but sweet guitar solos and beautiful vocal harmonies.

A self-described "gear freak,"[18] Ackerson's abiding interest in recording technology and studio experimentation led to a successful career as a producer.

[32] Ackerson also worked several times with the Jayhawks-associated supergroup Golden Smog,[33] which also included members of Soul Asylum, The Replacements, and Wilco, on their 2006 and 2007 albums Another Fine Day and Blood On The Slacks.

In 2006, Ackerson was asked by the Replacements to produce two songs for the Rhino Records retrospective set Don't You Know Who I Think I Was?, the tracks "Message To the Boys" and "Pool & Dive."

He kept his illness private and continued working, but revealed the diagnosis publicly after Pete Townshend of The Who wished him good health and a speedy recovery onstage during a St. Paul concert in September 2019.