"My grandmother, my Nana, came to pick us up ... and she said, 'Everybody put your seatbelt on.' And ... I go, 'Yeah, we don't want to wind up like Jeffrey!' It was just silence," Silverman recalled. "So that was the first time I bombed."
Silverman has been known to push the boundaries of political correctness, addressing sensitive topics in her stand-up such as ethnic stereotypes, racism, and rape.
"I really need more rape jokes in my act because rape jokes are kind of a trick in comedy and yet you never get in trouble for them because who's going to complain, rape victims?" she said in her stand-up. "They barely report rape, you think they are going to take the time to write a letter? As a victim of rape I found your joke inappropriate, cruel, and completely my fault."
"I'm never out to hurt someone," Silverman said. "It's never about making light of rape or the Holocaust or making light of AIDS. It's me being an idiot about thinking things that are serious."
After a long and public romance with comedian Jimmy Kimmel, Silverman is now dating a writer for the animated series, "Family Guy."
"His name is Alec. He's awesome. Super funny. Super cute," Silverman gushed.
Silverman admits she couldn't date someone who was not funny.
"Needing someone very funny really narrows the field down to freaks, but I lucked out," she said.
Are kids in her future?
"I love kids. I'm crazy about kids. I think I do. But I want to wait until it's all I want," she said.
Imagine what Silverman's kids will be like -- dancing like Snoopy and telling jokes until their arms itch.