Habib, who now hosts the monthly San Francisco stand-up show, Applesauce, and performs at various comedy venues in the city, including Cobb's, The Fillmore and Punch Line, remembered Gunn as a place where teachers were willing to support and foster student creativity.
"When I was a student and I first said I wanted to do stand-up, they took the risk, even though it could have been inappropriate," he recalled. "That's what makes the department special: They don't shy away from showing creative talent."
Lee, who recently relocated to Los Angeles from New York, has worked on MTV's Middle of the Night Show and hosts the podcast, "I Don't Know You," spoke of veteran Gunn Theatre Department teacher Jim Shelby as "the godfather of entertainment."
"His name will come up in the industry in conversations that aren't even related to Gunn," she said. "When I was a student, I didn't realize how powerful that department was or that it was so unique from other high schools. Mr. Shelby has been very influential in my early career."
Though they're contributing all proceeds from their show to the future of the department, Lee and Habib are also looking to the past and hoping their former classmates — those who've come home for Thanksgiving — will come out to see the show, making the night something of a high school reunion.
"It would be super cool and surreal if our class and people that age could make it; it would bring back some incredible memories," said Habib, who produced his first comedy shows while at Gunn. "It would be so much fun to see everyone in one room, staring at us and being like, 'Wow that person got a lot more attractive.'"
"On top of that, I hope current students and recent alumni come out," noted Lee. "I was inspired by students in the classes above me, and it would be awesome to connect with generations a little younger than us."
As for the content of the show, Habib described his comedy as "pretty clean ... so it really doesn't matter if it's a 40, 30 or 12-year-old in the audience. This is definitely a show that anyone can attend. There's no need for censorship."
"I am probably not as clean as you Nathan, but I'm not dirtier than anything on TV that kids have access to," Lee added. "I've done a lot about being in your 20s in New York, dating and sex, but I don't go for shock or consider myself a dirty comic. I generally take a survey of the room before I start and can alter things as necessary."
Like any creative process, Lee said, writing for stand-up takes time and effort; it's not as simple as going up on stage and telling jokes.
"Every day I try to write at least three new jokes," she said. "Then I try them and throw out the ones that don't work. I talk a lot about personal experience, things that have happened to me and things I've observed."
For example, she said, her recent experience getting a tattoo became source material for her comedy.
"It was a little one, but we had to make the tattoo artist redo it four times," she said. "In my stand-up, the tattoo became a metaphor for how I'm ready to commit to someone as soon as they change everything about how they are."
If Lee's style tends toward the personal and confessional, Habib describes his comic style as observational.
"A big achievement for me is to take subject matter that is pretty mundane and make it into a very humorous situation," he said. Naming Jerry Seinfeld as one of his primary inspirations, Habib described the satisfaction of drawing out the awkwardness in a given scenario.
"I find it really rewarding to write bits about things that people don't really joke about, like a chili cook-off, or what a sweet tooth means, or certain office behaviors, or people who bike to work. People who bike to work are not inherently funny, but I do my best to find the humor there. It's a fun challenge."
Both Lee and Habib admitted it's hard to describe one's own work, but found it easy to articulate how they see each other as comedians.
"If I had to describe Teresa, I would describe a great ball of energy," Habib said. "Her work is super personal and also hilarious. She's extremely funny."
"Nathan is very well-rounded and really great at telling stories," Lee said of Habib. "Even at 16 years old, he was always very controlled on stage. You know he's going to take you on a journey, it's going to be funny and it's going to circle back to the beginning somehow."
Recently, Lee quit her day job to do comedy full-time; Habib currently works at a high-tech company during the day but still finds a way to perform about 100 shows a year.
"It can work either way," Lee said, encouraging budding comics not to measure their success in financial terms.
"The landscape of stand-up is changing, and changing quickly," Habib added. "In the past, it was clear what comedy was. Now there are so many different mediums and industries that takes a little bit longer to figure out the niche to go into." Patience and trust, he said, have been key.
"Something I think you learn doing stand-up is that you don't pick your style; your style picks you. It's a process that takes time."
For Gunn grads home for the holidays, and for anyone else curious to check it out, Lee and Habib promise an evening of belly laughs to round off Black Friday. Bring your friends, your family and your sense of humor — but maybe leave that leftover turkey sandwich at home.
What: Gunn Alumni Comedy Night with Teresa Lee and Nathan Habib
Where: Little Theatre, Henry M. Gunn High School, 780 Arastradero Road, Palo Alto
When: Friday, Nov. 27, 8 p.m.
Cost: $5-$10. Tickets are available online and at the door. All proceeds go to the Gunn High School Theatre Department.
Info: Go to goo.gl/KIHt1x or goo.gl/P6sXD8.
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