STATEN ISLAND, N.Y. — Six months after deciding to go all in on comedy, a then-26-year-old Wellie Jackson found himself performing a set at Madison Square Garden in front of a packed crowd.
The born-and-raised Staten Islander had been invited by comedian Tu Rae Gordon, one of Jackson’s mentors, who was opening for R&B group New Edition. The experience was foundational for Jackson, a fledgling professional comedian at the time; but it was also validation he was embarking down a path he was always meant to be on.
Now 38 years old, Jackson has toured the country with comedy superstars Tracy Morgan and Tiffany Haddish; notched writing credits for series like TBS’s “The Last O.G.” alongside Morgan and Jordan Peele; and appeared on Netflix’s “Orange is the New Black” and Peacock’s “Girls5Eva.”
And that’s just a sampling of Jackson’s impressive resume.
Wellie Jackson performs a set at the Cutting Room. Jackson has been drawn to comedy since he was a young child. (Courtesy of Wellie Jackson)(Courtesy of Wellie Jackson)
‘JUST DO ONE SHOW’
When the Susan Wagner High School alum reflects on his trajectory, the signs that he should pursue comedy — and show business — were always there. He fell in love with comedy at a young age; his introduction to it came by way of episodes of “Def Comedy Jam” that he would watch with his dad and sister, as well as a cassette tape of a Richard Pryor set his dad encouraged him to check out during a long flight.
It didn’t hurt he was actually funny, too, which was constantly pointed out to him by other people.
So, when his dreams of being a pro athlete came to a grinding halt following a college basketball career-ending injury at 19, Jackson decided it was time to pivot.
After graduating from Manhattan Community College, and following a stint of jobs that included working at Sears in the Staten Island Mall, Jackson landed an internship at Sirius Radio (before it became Sirius XM Radio), which is where he met the…
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