During high school, Stipe lived in Collinsville, Illinois. Stipe found high school difficult; he said, "It was a very outgoing, flamboyant, loud school, and I hated everything about it. I was very, kind of afraid of a lot of things. In 1976 Stipe joined his first band, which lasted until the following year. While Stipe said the band was not spectacular, he acknowledged his bandmates had a major influence on him, introducing him to the music of The Stooges and The Velvet Underground.
Stipe graduated from high school in 1978, and enrolled at the University of Georgia in Athens, Georgia, as an art major, studying photography and painting.
All four members of R.E.M. dropped out of school in 1980 to focus on the band. Stipe was the last to drop out, as he still hoped to pursue a career in art history and photography. The band issued its debut single, "Radio Free Europe", on Hib-Tone. The song was a college radio success and the band signed to I.R.S. Records for the release of the Chronic Town EP one year later. R.E.M. released its debut album Murmur in 1983, which was widely acclaimed by critics. Stipe's vocals and lyrics received particular attention from listeners. The band's second album, Reckoning, followed in 1984.
R.E.M. traveled to England to record its third album Fables of the Reconstruction (1985). The band members found the sessions unexpectedly difficult, and were miserable due to the cold winter weather and poor food. Stipe also had a disagreement with producer Joe Boyd over his vocals: Boyd wanted the vocals to be clear, but Stipe "was still in his period of not wanting the vocals to be clear, so he argued against making them louder or brighter or clearer", the producer said. The difficult situation brought the band to the verge of break-up. Even after the album was released, relationships were tense within the band. Stipe said of the period, "I was well on my way to losing my mind". Stipe gained weight and his behavior became more eccentric; he shaved his hair into a monk's tonsure, and later, dyed it yellow with egg yolk. Antagonisms between Stipe and Mills came to a head in 1985. Mills said later, "Michael and I didn't get along in a lot of ways for a few years. We were very different people [. . .] Michael was trying to deal with being a really shy person thrust to the front of the band. And I was trying to deal with how somebody had an attitude when it was unnecessary." The bandmates had a talk to "clear the air", and resolved their differences.
This might be really naïve, but my number one reason was – this is incredibly naïve, in retrospect – but I really felt like there are a lot of people who might respect me, for whatever reason, because of the music or just because I’m a celebrity, that think that the AIDS story about me might impact them in the way they handle their own private affairs, or in the way they thought about people who were HIV positive or who had AIDS. And, number two, I felt like it was a ludicrous claim and I didn’t feel like sinking to kibbles-and-bits journalism to even respond to it. It was spawned from a ridiculous series of little things and I didn’t feel like it was worth answering.
According to Stipe, he did not start the rumor and he does not know who did.
Not that I can tell. I wore a hat that said 'White House Stop AIDS'. I’m skinny. I’ve always been skinny, except in 1985 when I looked like Marlon Brando, the last time I shaved my head. I was really sick then. Eating potatoes. I think AIDS hysteria would obviously and naturally extend to people who are media figures and anybody of indecipherable or unpronounced sexuality. Anybody who looks gaunt, for whatever reason. Anybody who is associated, for whatever reason – whether it's a hat, or the way I carry myself – as being queer-friendly.
Stipe had planned a collaboration with Nirvana's Kurt Cobain in 1994, but did not manage to compose or record anything before Cobain's death. Stipe was chosen as the godfather of Kurt Cobain and Courtney Love's daughter, Frances Bean Cobain.
Stipe was once very close to fellow singer Natalie Merchant and has recorded a few songs with her, including one entitled "Photograph" which appeared on a pro-choice benefit album entitled Born to Choose and they have appeared live with Peter Gabriel singing Gabriel's single "Red Rain".
Himself a vegetarian, in the mid 1990s Stipe opened a vegetarian restaurant and juice bar, called Guaranteed, in Athens, Georgia.
In 1998, Stipe published a collection called Two Times Intro: On the Road with Patti Smith and worked on Single Cell Pictures, a film production company which released several arthouse / indie movies.
In a 2001 Time interview, Stipe described himself as a "queer artist" and revealed that he had been in a relationship with "an amazing man" for three years at that point. In previous interviews he has described himself as "an equal opportunity lech and said he does not define himself as gay, straight, or bisexual, but that he was attracted to and had relationships with both men and women.
Stipe contributed haiku for a book published by Soft Skull Press called The Haiku Year.
In 2006, Stipe released an EP that comprised six different cover versions of Joseph Arthur's "In The Sun" for the Hurricane Katrina disaster relief fund. One version, recorded in a collaboration with Coldplay's Chris Martin, reached number one on the Canadian Singles Chart.
Also in 2006, Stipe appeared on the song "Broken Promise" on the Placebo release Meds. Continuing his non-R.E.M. work in 2006, Stipe sang the song "L'Hôtel" on the tribute album to Serge Gainsbourg entitled "Monsieur Gainsbourg Revisited" and appeared on the song "Dancing on the Lip of a Volcano" on the New York Dolls album "One Day It Will Please Us to Remember Even This".
"That voice. It's an extraordinary voice," said U2's Bono in 2003. "I often tell him I think he's a crooner, and he doesn't like that very much. But it is sort of one part some sort of Bing Crosby '50s laid-back crooner, and one part Dolly Parton," he added, laughing.
Stipe insisted that many of his early lyrics were "nonsense", saying in a 1994 online chat, "You all know there aren't words, per se, to a lot of the early stuff. I can't even remember them." In truth, many early R.E.M. songs had definite lyrics that Stipe wrote with care. Stipe explained in 1984 that when he started writing lyrics they were like "simple pictures", but after a year he grew tired of the approach and "started experimenting with lyrics that didn't make exact linear sense, and it's just gone from there." In the mid-1980s, as Stipe's pronunciation while singing became clearer, the band decided that its lyrics should convey ideas on a more literal level. Mills explained, "After you've made three records and you've written several songs and they've gotten better and better lyrically the next step would be to have somebody question you and say, are you saying anything? And Michael had the confidence at that point to say yes . . . Stipe incorporated more politically-oriented concerns into his lyrics on Document and Green. "Our political activism and the content of the songs was just a reaction to where we were, and what we were surrounded by, which was just abject horror," Stipe said later. "In 1987 and '88 there was nothing to do but be active." While Stipe continued to write songs with political subject matter like "Ignoreland" and "Final Straw", later albums have focused on other topics. Automatic for the People dealt with "mortality and dying. Pretty turgid stuff", according to Stipe, while Monster critiqued love and mass culture.
Stipe has made a number of acting appearances on film and on television. Stipe appeared in an episode of The Adventures of Pete & Pete as an ice cream man named Captain Scrummy. Stipe has appeared as himself with R.E.M. on Sesame Street playing a reworked version of "Shiny Happy People" called "Furry Happy Monsters", and appeared in an episode of The Simpsons titled "Homer the Moe", where R.E.M. was tricked into playing a show in Homer Simpson's garage.