About a year into Harry’s comedy career, a then unknown but very well respected Jerry Seinfeld approached Harry. He said, “You’re a good writer,” and added, “I don’t just say that to anyone.”

About the same time, Joan Rivers also caught Harry’s act. She invited him to hang out in her dressing room before her next few shows at the Diplomat Hotel in South Florida.

Over the years, Harry has toured the country, opening for many  big name comics. This includes Jerry Seinfeld, Tim Allen, Dennis Leary, Andrew Dice Clay, Paul Reiser, Pat Paulson, Drew Carey (who actually opened for Harry) and many more.

He also became friends with Ray Romano and Richard Jeni. And Harry has opened for both in numerous theaters and clubs across the country, including Carolines in New York City.

In the late 80’s and early 90’s, Harry was featured on many national TV shows. Among them, were VH1 Stand-up Spotlight with Rosie O’Donnell, Comedy on the Road with John Byner, and Carolines Comedy Hour on A&E with Richard Jeni, which Harry also wrote for. In addition, Harry took home a nice check for coming in 3rd place on America’s Funniest People.

Harry was also a regular at New York’s top comedy clubs including The Improvisation, The Comic Strip, and The Comedy Cellar. In addition, Bill Maher took a liking to Harry’s humor, and regularly gave him spots at Catch a Rising Star.