Guitarist Mike Connell formed the band in 1984 along with his brother David Connell on bass, Doug MacMillan on vocals, and future filmmaker John Schultz on drums. This initial four-person line-up was quickly supplemented by the addition of George Huntley on second guitar, keyboards, and vocals. Around the same time, former Johnny Quest drummer Peele Wimberley replaced Schultz, finalizing the "classic" line-up of the band.

An early version of “Darker Days,” recorded by the band’s initial four-piece lineup, appeared on the North Carolina indie compilation More Mondo in 1984. A re-recorded version of “Darker Days” provided the title track to the band’s debut album, which was produced by fellow North Carolinian Don Dixon and released in 1985 on Elvis Costello's Demon Records in the UK and the band’s own Black Park Records label in the U.S., with slightly different tracklistings for each country. In addition to the title track, one of the most notable songs on the album was “Hats Off,” an attack on then-President Ronald Reagan. After the release of the Darker Days album, the band re-recorded a more aggressive take of “Hats Off” for a 12” single, which was the second Connells release on Black Park, and the last until 2000. During this period, videos for the songs “Seven” and “Hats Off” were aired on MTV’s 120 Minutes program.

After touring heavily behind Darker Days, the Connells re-entered the studio in 1986 with Dixon and R.E.M. producer Mitch Easter to record their second album, Boylan Heights. The decision to work with Easter continued to perpetuate the comparisons to R.E.M. According to some music critics, Mike Connell’s songwriting reached a peak on Boylan Heights, as the songs from this album would provide most of the foundation for the band’s live show for the remainder of their career. The opener, “Scotty’s Lament,” featured the most explicit Celtic influence in the band’s songbook, while the chorus lyric “I delight in my despair” satirized the band’s early image as doom and gloom merchants a la Morrissey and The Smiths. Although notable is that the lyrics for that song originally included the sardonic twist, "I delight in your despair."

“Choose a Side” incorporated synths (played by Huntley), and “Over There” featuring an ironic military trumpet counter-melody. Closing ballad “I Suppose” was a haunting tribute to the Raleigh inner-city neighborhood of Boylan Heights. Although the band shopped Boylan Heights to various labels, the major record companies, including Columbia Records, which expressed some mild interest, passed on it; the record was ultimately released in 1987 on mid-major TVT Records, which had made its name releasing a series of "Tee Vee Toons" television theme song compilation CDs. TVT would prove to be no commercial match for R.E.M.'s own mid-major label, I.R.S. Records, and over the next decade, The Connells would engage in a series of disputes with the label, on at least one occasion suing, unsuccessfully, to break their recording contract.

Despite the problems with TVT, Boylan Heights was a substantial college radio hit, and The Connells continued to tour relentlessly. During this period, both Connell and Huntley began to move away from their twelve-string Rickenbackers towards six-string Fender and Gibson guitars, leading to a heavier, less folky sound, although elements of the band's patented jangle were still audible on "Hey Wow," the lead single from Fun and Games, the 1989 follow-up album. Other songs, such as "Something to Say" and "Upside Down" were heavier, featuring power chords, as well as the most self-lacerating lyrics to date from Connell. Fun and Games also saw Huntley's role as a songwriter grow; after contributing one song each to Darker Days and Boylan Heights, Huntley wrote or co-wrote four tracks on Fun and Games, with the anthemic "Sal" quickly becoming one of the most popular songs in the band's live set. CD pressings of Fun and Games included a bonus track, "Fine Tuning."

Fun and Games was quickly followed in 1990 by One Simple Word, which was recorded in Wales with U.K. producer Hugh Jones. Jones had previously produced various British bands that the band had admired. Despite the high quality of the songs and improved playing by the band, notably on the Connell-MacMillan collaboration "Stone Cold Yesterday" and Connell's own "Get a Gun" which were both college radio hits with videos, the band struggled to reach a higher level of success. This album saw the band stretch their sound and playing further, as on Connell's debut as a lead vocalist, the plaintive ballad "Waiting My Turn," which featured a cor anglais, but also saw the reworking of two songs that dated back to the Darker Days era, "Too Gone" and "Take a Bow." Some critics have contended that the album/tour/album cycle was by this point outstripping Connell's ability to compose new material. This is why the increasing contribution of other songwriters in the band becomes important as lead vocalist, Doug MacMillan also contributed a song, "Another Souvenir," that he had written on his own.

After a three-year recording hiatus, which included more legal jousting with TVT Records, a rejuvenated Connells released Ring in 1993. The lead single, "Slackjawed," was another college radio hit in America, but the follow-up single, "'74-'75," another Celtic-influenced ballad, took off in Europe, and became a top-20 hit across the continent, leading to the band touring extensively in Europe and opening stadium shows for the likes of Def Leppard. "'74-'75" won numerous European music awards in the mid-1990s, leading to greater financial and radio success than the band had known to that point. "'74-'75" also appeared in the 1995 film Heavy. However, while European music fans made Ring a platinum record outside the United States, such high level success in America remained elusive. Ring also marked the debut of David Connell stepping up as a songwriter by co-writing a song for the record, "Hey You." MacMillan also wrote additional songs for the record. The band also played "Slackjawed" on Late Night with Conan O'Brien.

1996's Weird Food and Devastation failed to build on the momentum established by its predecessor. Weird Food was a much starker record than the more melodic Ring. Weird Food and Devastation was produced by the band's longtime soundman, Tim Harper, later known for his production work for Whiskeytown. The title of the album reportedly alluded to the band's impressions of Europe during their seemingly endless tours there in support of "'74-'75," and Connell's songwriting took a quirkier turn, with the lyrics to "Adjective Song" beginning: "Bigger. Better. Smarter. Cleaner. Nicer. Younger. These are the words we use to describe." "Friendly Time" abandoned coded attacks on Ronald Reagan for coded attacks on rock critics such as Robert Christgau and J.D. Considine. Lead single "Maybe" showed that Connell hadn't lost his ability to compose anthemic pop songs, but his remaining songs on the album were often odd and dissonant compared to his previous work, and he contributed only six out of the fourteen songs on the album.

The band recorded music videos for "Maybe" (a parody of the Burt Reynolds film Deliverance) and "Fifth Fret" (which was a parody of Psycho). The band was invited to perform for a second time on Late Night with Conan O'Brien where they performed "Maybe."

In 1998, the band released Still Life, which marked their final album for TVT. Still Life marked a departure from the harder sound of Weird Food and Devastation with an overall softer feeling. Mike Connell's contributions to the record included a long-standing song with the band that was originally known as "Brown," which was re-titled "Dull, Brown, and Grey." The album included contributions from Peele Wimberley "It's Gonna Take a Lie" and "Bruise."

The band released Old School Dropouts on the revived Black Park Records label in 2000. The band recorded the record themselves and promoted it sparingly in the American South. The song "Washington" received some airplay on alternative radio.

Since then, Peele Wimberley and George Huntley have left the band. Wimberley briefly played with another band called Parklife, and then moved to Los Angeles to pursue interests in Hollywood and in electronic music. He is currently a member of the Los Angeles band, The Lamps. David, who lost his first wife to cancer, subsequently remarried and has a side interest in painting and art shows, and brother Mike is practicing law in Raleigh. Huntley is now selling real estate and working part time at the University of North Carolina music department. Peele Wimberley was replaced on drums by Steve Ritter; after several years Ritter was soon replaced by Chris Stevenson on drums, and Mike Ayers took George's place on lead guitar. The new lineup recorded the album Old School Dropouts.

The band is also in negotiations for a re-release of out-of-print albums, as well as a release of the band's first official compilation, which will likely come from Rykodisc or Rhino Records. Due to family and career commitments, the band currently plays only a handful of shows each year, normally in the southern part of the United States, usually at benefit concerts and music festivals.