Reynolds grew up in Wood Village, Oregon (near Portland), where, by his own account, his upbringing was "tragic." His father, Jack, died when Reynolds was an infant, leaving his mother to raise three children by herself. Much of Reynolds' stage work has centered around his struggle as an adult to heal the psychic scars left by his mother's alcoholism and abusive behavior.

After graduating from Portland State University with a BS in philosophy, he worked as a production assistant at a local TV station, wrote an entertainment column for Willamette Week, and published a short-lived but notorious satirical newspaper called The Oregonite. With no previous stand-up experience, Reynolds entered the 1980 Portland Comedy Competition and walked away with the grand prize: a one-way ticket to San Francisco, then a mecca for aspiring comics. Honing his skills with the likes of fellow unknowns Paula Poundstone and Dana Carvey, Reynolds achieved the status of national headliner by the mid-1980s and made the obligatory move to Los Angeles to further his career.

In 1989, frustrated in his attempts to break into film and television and growing dissatisfied with the strictures of the stand-up form, Reynolds fled Hollywood and returned with his wife to northern California to start a family and write his first one-man show, Only the Truth Is Funny. A mélange of brutally honest personal confession, gut-wrenching childhood remembrances, and episodes of high hilarity drawn from his own life, the show opened in 1990 at The Improv in San Francisco, where it played to capacity crowds for the better part of a year and attracted the attention of Rollins & Joffe, the management team responsible for the careers of Woody Allen and David Letterman, among others. Under their aegis, Only the Truth Is Funny was reborn as a theatrical production, garnering rave reviews during an extended run in San Francisco and subsequent stints in Los Angeles and Off Broadway. In 1993, it was filmed as a Showtime special, for which Reynolds received an Emmy Award nomination for Outstanding Individual Achievement in Writing. Only the Truth Is Funny was ultimately released on audio CD (by Gang of Four) and in book form (by Hyperion).

Reynolds launched a second one-man show, All Grown Up...and No Place to Go, in 1995. Picking up where Only the Truth... left off, the new production touched on the themes of parenting, marital problems, couples therapy, and other peaks and valleys of adulthood as experienced by a self-described "asshole" who "never really wanted to grow up in the first place."

Though it fell somewhat short of the critical acclaim accorded Only the Truth Is Funny, All Grown Up...and No Place to Go proved to be another crowd-pleaser, enjoying a long, successful run in San Francisco and earning Reynolds a development deal with CBS. The resulting sitcom, Life...and Stuff, starring Reynolds and Mork and Mindy alumna Pam Dawber as a husband and wife coping with a troubled marriage, premiered as a CBS summer replacement series in 1997, only to be yanked after two episodes.

Since then, Reynolds has struck development deals with other TV networks, including HBO, and penned several screenplays, as yet unproduced. He is currently working on a new one-man show tentatively entitled Happiness.