Meanwhile, Michael Stipe really liked Sweet's tape, and also played it for his sister Lynda Stipe. She invited Sweet to come open for her band Oh-OK in Athens. In the late spring of 1983, just before graduating from high school, he went down to Athens, and within a week was a member of Oh-OK, who recorded their E.P. Furthermore What that August with him onboard. While a member of Oh-OK, Sweet also found time to collaborate with Michael Stipe on the Community Trolls songs.
[Stipe] was the real powerhouse behind it. I was pretty tentative in those days. We just sat around, Michael went through the little book he wrote lyrics in, with me just kind of strumming along behind.
Sometime in the autumn of 1983, Stipe and Sweet recorded their three song demo, but only "Tainted Obligation" has been released from that session. Stipe plays accordion and sings lead vocals, and Sweet plays acoustic guitar and does harmony vocals. Rolling Stone describes the song as "enchanting" with "harmonies as pretty as you can imagine.
In 1986, "Tainted Obligation" was slated for, but was not ultimately released on, the Demon Records compilation album Don't Shoot, which featured such artists as John Doe, Top Jimmy & The Rhythm Pigs, The Divine Horsemen and Clay Allison.
In the early 1990s, the song would surface as "Tainted Obligations" on R.E.M. bootlegs such as Stab It and Steer It and Wolves, Lower.
The song was finally released officially on the 2002 Matthew Sweet compilation To Understand: The Early Recordings of Matthew Sweet.
"Six Stock Answers" was used in a low budget forty-five-minute Super-8 film called Just Like A Movie, shot in September 1983 in Athens by New York Rocker magazine photographer Laura Levine, a friend of the members of R.E.M. One scene in the film, a parody of the "Subterranean Homesick Blues" sequence in D.A. Pennebaker's Bob Dylan documentary Dont Look Back, shows Michael Stipe wearing a skirt and tights flipping placards with the song's lyrics, "Six stock answers to 74,000 questions" repeated ad nauseam. Just Like a Movie's plot has two rival bands performing on the same night, leading up to the climax question of "Which band is everybody going to go see?" R.E.M. biographer Marcus Gray believes it is likely that the Stitchcraft show, including the Community Trolls' set, was used in the film and provided the answer to this question.
Sweet began distancing himself from other people in the Athens, Georgia music scene and in 1984 quit Oh-OK; in 1985, he got a record deal with CBS Records and moved to New York City. Sweet was accused of selling out and using his Athens connections to get a record deal and leave. Sweet maintains that when he went to CBS he never claimed to have anything to do with Athens, so that nobody could say he used the town. He says that after months of living in Athens he realized things weren't as happy there as everyone pretended, and that there was backstabbing going on. In 1993 he said:
Things really turned dark there when R.E.M. got famous, because everyone wanted that fame so bad. Maybe I wanted it too, but I had this musical goal all of my own and wasn't going to go along with the way it was done there.
Everybody was telling him that he should be touring and building up a following before doing his record, like R.E.M. had done. However, more than making the record itself and becoming a rock star, Sweet's main motivation was to get money to buy studio gear.
R.E.M., for their part, held no hard feelings towards Sweet. Peter Buck has said, "The guy wanted to make records. I don't see anything wrong with that." Still, Sweet said in 1995 that he and the band were no longer very close, and when asked about the possibility of him touring with them, he replied he wasn't sure if the band would want to.
In 1996 or 1998, Sweet recorded with R.E.M.'s Mike Mills on the song "The Ballad of El Goodo," on the Big Star tribute Big Star Small World, which was finally released in 2006. Sweet sang vocals (and possibly played guitar), Mills played bass, and Jody Stephens played drums.