Berry was born in Duluth, Minnesota, to Don and Anna - their fifth child. At three years old, Berry moved with his family to Wauwatosa, Wisconsin, a suburb of Milwaukee, where they would remain for the next seven years. In 1968, they were on the move again, this time to Sandusky, Ohio, on the banks of Lake Erie.

In 1972, the Berry family made their final move, to Macon, Georgia. There he met bassist Mike Mills at high school, and they played together in several different bands. Berry and Mills moved to Athens, Georgia in 1978, where they met Michael Stipe and Peter Buck. R.E.M. was formed in 1980. In 1995, Berry collapsed on stage while touring, due to a brain aneurysm. He left R.E.M. in October 1997, citing personal reasons. In 2000 he recorded for Tourette Syndrome Charity Album Welcome Companions.

Stipe said that when Berry approached them and begged them to let him leave, he said to the band that he could compromise and record with them, which would make him sad, but he didn't want to do any interviews or tours. Stipe said, "I just love the guy too much to see him sad," and thus they let Berry leave the band for the sake of his own happiness.

After his departure, Berry had brief reunions with his former bandmates. Firstly, in 1999, where he jumped on stage to embrace with his old band members. In 2003, Berry joined the band for two songs at their October 10 show in Raleigh, North Carolina, the second-to-last date of their 28-show fall tour. Despite this, bandmembers Peter Buck and Michael Stipe said that they do not expect Berry to make a reappearance any time soon and that he remained firm on his decision to retire.

However, on 8 October 2005 Berry came out of retirement for a second time. The four original members of R.E.M. reformed at the weekend to perform at the wedding of one of their roadies. The four played seven songs at Kingpins Bowl And Brew in Athens, Georgia, at technician Dewitt Burton's wedding.

Less than sixth months later and in the very next performance of R.E.M. together as a band, Berry rejoined R.E.M. for a third time. On April 1, 2006, Berry, Mike Mills, and Michael Stipe joined Peter Buck, who was touring with The Minus 5, on stage in Athens, Georgia during the intermission of the band's final tour date to perform "Country Feedback" from R.E.M.'s album Out of Time.