“I want [my guests] to know right away this is going to be fun,” Mr. Ellin, 36, said last Thursday, after wrapping a live broadcast of his show. Sitting in the basement bar of Chelsea’s Gotham Comedy Club, Mr. Ellin, who bears a passing resemblance to both Jeremy Piven and Jimmy Kimmel, depending on the angle, said he has high hopes for LateNET, which launched last May on Paltalk, the Internet’s largest video chat community.

“There’s something about closeness that really makes everything kind of surreal,” beamed Mr. Ellin of working with his comedic heroes. His past guests include Fran Drescher (“She was very flirtatious!”); Late Show’s Paul Shaffer, who composed an impromptu theme for LateNET; and SNL’s Darrell Hammond, whose Al Sharpton impression proved a hit with viewers.

Mr. Ellin is a comedian himself—he did his first stand-up show at 15—but hosting has come even more naturally to the Boston native. “When I was a kid, people would always tell me to shut up because I was asking too many questions,” he said. “I’m naturally a very inquisitive person. I’d rather talk about someone else than talk about myself. It’s more comforting.”

LateNET With Ray Ellin is broadcast live from the Gotham Comedy Club, 208 West 23rd Street. The show can also be viewed on Paltalk.com, where upcoming schedule information will be updated soon.