Wilson has collaborated with a diverse[3] range of artists, including Pink, Celine Dion, Leon Bridges, Mitski, Claud, Halsey, Weezer, Panic!

at the Disco, My Morning Jacket, Dierks Bentley, John Legend, Joy Oladokun, Laufey, and many others.

[6] On February 4, 2024, Wilson won the Grammy for Best Country Song for “White Horse,"[5] which he co-wrote with Chris Stapleton.

On November 20, 2024, Wilson won his first CMA Award for Song of the Year for “White Horse,"[5] which he co-wrote with Chris Stapleton.

After Trip Shakespeare's breakup in 1992, Wilson and Munson joined with drummer Jacob Slichter to form Pleasure, a trio that was later renamed Semisonic.

David Fricke wrote in a year-end Rolling Stone article on the notable albums of 1996, "Great Divide is that rare '96 beast, a record of simple but sparkling modern pop, rattling with power-trio vitality."

It was their 1998 release, Feeling Strangely Fine, however, that brought the band to widespread national and then international attention and success.

Powered by Wilson's songs "Closing Time", which was a number-one hit on the Modern Rock charts for thirteen weeks in the spring and summer of 1998, the follow-up single "Singing in My Sleep", and "Secret Smile", a breakthrough hit for the band internationally, Feeling Strangely Fine attained platinum sales status in the U.S. and U.K. "Closing Time" received a 1999 Grammy nomination for Best Rock Song[11] and has become an enduring pop-culture reference point for the late 1990s.

Slichter's memoir, So You Wanna Be a Rock & Roll Star, provides a detailed account of the band's adventures and misadventures in the music business.

Produced with Rick Rubin, Free Life was recorded in Minneapolis and Los Angeles and includes performances by Tracy Bonham, Sheryl Crow, Jason Lader, Gary Louris, Natalie Maines, Benmont Tench, and a number of Minneapolis-based musicians including multi-instrumentalist and frequent Semisonic sideman Ken Chastain, Eric Fawcett, John Hermanson, Joanna James, Mason Jennings, Steve Rhoem, Joe Savage, as well as Wilson's Semisonic bandmates Munson and Slichter.

Club writing, "the star of the show here is Wilson's remarkable instinct for creating gorgeous songs, and his unabashed, obvious joy in doing so.

"[12] The song Breathless became a big hit in Greece (and other Balkan countries[13]) and Dan Wilson performed it at the 2009 MAD Video Music Awards.

In describing the album, Wilson said, "The songs are about being left alone, not wanting to lose someone, about desperately wishing for connection and togetherness.

"Words and Music by Dan Wilson" has come to Hotel Cafe, Room 5 and Largo in Los Angeles, Joe's Pub and City Winery in New York, World Cafe Live in Philadelphia, Jammin' Java in DC, Rams Head in Annapolis, The Cedar Cultural Center in Minneapolis, the Fitzgerald Theater in Saint Paul,[24] Schubas Tavern in Chicago, Berklee College of Music's Red Room at Cafe 939 in Boston, and the Red Barn concert series in Northfield, MN.

[25] Wilson's thoughts about songwriting and the creative process are also captured in his series, Words & Music in Six Seconds, which was originally launched on Vine and is now regularly posted on Instagram, Twitter, and Facebook.

"[26] In November 2020, he released the Words + Music in 6 Seconds deck, a collection of cards written and designed by Wilson based on his Instagram series.

In describing her co-writing with Wilson, Adele said, "Dan had me on my hands and knees, crying my eyes out - there's just something about him that made me completely open up as a composer.

In the 2006 film Dixie Chicks: Shut Up and Sing, Wilson speaks on camera about his experience as a co-writer on this album, especially in regard to helping the Dixie Chicks make an artistic response to their rejection by radio and a large swath of their fans in the wake of the band's statements about President Bush and the Iraq War.

One of the songs he co-wrote for this album, "Easy Silence", appears on Free Life, with Dixie Chicks singer Natalie Maines singing harmonies.

He was represented by Thomas Barry Fine Arts in Minneapolis, and his works are included in numerous private and corporate collections.