Founded in Cleveland Ohio by Tom King (originally of The Starfires), and named by the band manager's wife, the Outsiders' early lineup also included Mert Madsen (bass, harmonica) from the original Starfires along with singer Sonny Geraci. The band is best known for “Time Won’t Let Me,” which reached #5 on the Billboard Hot 100 charts in April 1966, selling over a million copies and spending 15 weeks on the chart. The song was later covered by Iggy Pop on his 1981 album Party, and the Smithereens had a hit with the song in 1994.

The band's other hit records included "Girl in Love", "Respectable," and "Help Me, Girl." The Outsiders drum head displayed in the Rock and Rock Museum in Cleveland was designed by original bass player Mert Madsen. Band founder Tom King passed away due to congestive heart failure at a nursing home in Wickliffe, Ohio on April 23, 2011 at the age of 68.

In 2020, with rights to the band name now claimed by latterday drummer Howard Blank, the Outsiders signed a record deal with local Pacific Records and announced plans for a new original album featuring Blank with San Diegans like singer Lori Wilson and bassist Matt Simpson, as well as latter-day Mamas and the Papas singer Laurie Beebe Lewis, Brooklyn singer Eli Holland, guitarist Mel Vernon, keyboardist Yasha Susoeff, and sax player Jim Bruno. This band was renamed Howard Blank’s The Outsiders.

The release included two previous Outsiders hits, “Time Won’t Let Me” and “Respectable,” a cover of Climax's “Precious and Few,” and new tracks “True Love,” “Fly Me Away,” and “Everyone Has Gone.”

Howard Blank's latterday stewardship of the band has been disputed by other former band members.