About a year into Harry’s comedy career, a then unknown but very well respected Jerry Seinfeld approached Harry and 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 and invited him to hang out in her dressing room before her shows at the Diplomat Hotel in South Florida.
Over the years, Harry has toured the country, opening for comics like Jerry Seinfeld, Tim Allen, Dennis Leary, Andrew Dice Clay, Paul Reiser, Pat Paulson, Drew Carey (who actually opened for Harry) and many more.
He became friends with Ray Romano and Richard Jeni and 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 VH1 Stand-up Spotlight with Rosie O’Donnell, Comedy on the Road with John Byner, Carolines Comedy Hour on A&E with Richard Jeni, (which Harry also wrote for) and was a prize winner on America’s Funniest People.
He 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 became a big fan of Harry’s, and used to put him on at Catch a Rising Star
But all of that was merely a prelude to Harry’s next move.