Kal Penn's eclectic career path has had twists and turns that rival any blockbuster movie, taking him from Hollywood to the White House to primetime television.
As an actor, Penn has starred in the "Harold & Kumar" comedy film franchise and on TV shows like "House" and "Designated Survivor." And, in 2009, Penn took a break from acting to take a job in President Barack Obama's administration, serving as an associate director in the White House Office of Public Engagement until 2011. Now, Penn's career is taking a new turn, as a TV show he co-created and stars in, a new sitcom called "Sunnyside," airs on NBC on Thursdays.
Starring in a primetime show where he's also a writer and executive producer is a sign that the 42-year-old Penn has established a strong foothold for himself as a creator and performer in the entertainment industry. But 15 years ago, Penn was still establishing himself as an actor, which often meant working various side-jobs — Penn spent time waiting tables, bartending, even working as a telemarketer before breaking out as an actor — to support himself.
In 2004, Penn starred in "Harold & Kumar Go to White Castle," a movie that would eventually help make the actor a household name, but which also "tanked at the box office," Penn tells CNBC Make It. The movie made less than $24 million in theaters worldwide (it didn't even crack the top 100 highest-grossing movies of 2004, according to Box Office Mojo), though it later found a bigger audience through word-of-mouth and DVD sales that helped launch two sequels.
"I never got a big paycheck from 'Harold and Kumar Go to White Castle,'" says Penn, who adds that he and the film's other lead star, John Cho, each made a gross salary of $75,000 for the movie.
What's more, Penn took home much less than that amount after he'd finished divvying up his movie salary among his team of agents and other representatives. "You deduct your taxes, 10% to your agent, 15% your manager, 5% to your lawyer, your publicity fees and then your rent," Penn says. "And it averages out to probably about five-and-a-half months of living expenses once you've paid everybody and paid your taxes."
Penn says a working actor is likely to keep "maybe 30% of your paycheck" after paying taxes and a team of representatives (meaning he would have been left with roughly $22,500 from his salary on the first "Harold & Kumar" film).
And, in general, he adds, actors typically make money "in these weird chunks" depending on what projects they're able to book at any given time. That's why many actors, especially those just beginning their careers, have to work a series of side hustles in order to support themselves.
The problem Penn ran into after getting his salary for "Harold & Kumar Go to White Castle," though, was that he hadn't even made enough money from the movie to support himself for half of a year, but between that film and his previous work (he had a supporting role alongside Ryan Reynolds in 2002's "Van Wilder"), Penn had become enough of a recognizable actor that he suddenly had trouble landing any service industry jobs to boost his income.
"You want to get a job to pay your rent, but you find out that, you know, you did 'Harold & Kumar Go to White Castle,' and that means that you can't get a job at Jamba Juice," Penn tells CNBC Make It. The reason, Penn says, is that service industry employers worry that even a somewhat recognizable actor could become a distraction in the workplace.
"If customers are stopping to talk to you about a project you did, then why would [an employer] hire you when they could hire somebody who might not be recognized?" Penn reasons.
It was a nerve-wracking Catch-22 for Penn: his acting career was starting to take off, but he still wasn't making enough money from Hollywood gigs to cover all of his living expenses, and his burgeoning fame made it more difficult for him to get a side job. "The tricky thing was there's no guarantee that you're gonna get another acting job, and all of a sudden Starbucks won't hire you," Penn reiterates, adding: "Most of the service jobs, like waiting tables, bartending and stuff that I'd done before, I couldn't get."
Fortunately for Penn, his acting career did not stall out, and he continued getting acting jobs, including landing small roles in movies like 2005's "Son of the Mask" and "Superman Returns" in 2006. And, as "Harold & Kumar Go to White Castle" eventually established a more mainstream following after being released on DVD, Penn landed multi-episode jobs on TV shows like "24" and "How I Met Your Mother" while also releasing the sequel film "Harold & Kumar Escape from Guantanamo Bay" in 2008.
While Penn no longer has to rely on side jobs to bolster his Hollywood earnings (he's made enough money from acting that he was able to buy a home in Los Angeles for nearly $1.2 million at the end of 2007), he talked to CNBC Make It about some of the best and worst part-time jobs he had to take while trying to establish his acting career.
"Telemarketing was awful. I hated that job. But, you know, it paid the bills for a little while," says Penn, who adds that he took a telemarketing job thinking it could serve as "an acting exercise" where he could try role-playing different characters while talking to people on the phone all day.
"That was not the case," Penn explains. "It was very shady. And it seemed like we were calling people on fixed incomes to ask for donations. So, I quit very shortly after I started."
While Penn still sees standard service industry jobs like waiting tables and bartending as "paying your dues" in the entertainment industry, he says his favorite side-job was slightly more physically intense.
"My favorite job was working on a farm," he says. "One summer, I went back to New Jersey, where I grew up, and worked on a farm all summer. And I was ripped by the end of that summer, let me just tell you."
"Sunnyside" airs Thursdays at 9:30pm ET/PT.
Disclosure: NBC and CNBC are both owned by the same parent company, NBCUniversal.
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