Wolfberg was a schoolteacher before launching a full-time comedy career in 1979. Wolfberg attended Queens College, where he received a master's degree in clinical psychology.

Wolfberg began his comedy career in New York City at the Comic Strip. Although he always wanted to be a comedian, he auditioned as a singer, playing his Martin guitar. Fortuitously, his audition piece was the Comic Strip's owner's favorite song: "American Pie." Wolfberg appeared twice on The Tonight Show. In addition, he was a frequent guest on The Merv Griffin Show, The Pat Sajak Show and The Arsenio Hall Show. He starred in his own half-hour comedy special on HBO in 1990.[2] He also had a recurring role as Gooshie on NBC's Quantum Leap, and in April 1993 Entertainment Tonight aired "A Day in the Life of Dennis Wolfberg," focusing on his relentless touring schedule.[citation needed]

He headlined at comedy clubs across the country as well as working in Las Vegas and Atlantic City on a regular basis. He was twice named America's top male comic in votes by club-goers and owners nationwide. In 1990 he won an American Comedy Award as best male stand-up.