The Untold Truth Of Kal Penn

When it comes to diverse careers, few Hollywood actors can match Kal Penn. One minute he's starring alongside John Cho as a modern-day Cheech and Chong in the White Castle-obsessed stoner comedy franchise "Harold and Kumar." The next, he's serving as the White House Office of Public Engagement's Principal Associate Editor in the Obama administration!

While his stint in the West Wing only lasted from 2009 to 2011, Penn has continued to flit between the worlds of politics and showbiz, serving as co-chairman of the 44^th's successful re-election campaign, delivering a speech at the Democratic National Convention and offering his support for Hillary Clinton, Bernie Sanders and Joe Biden while also working on projects titled "Dementamania" and "Untitled Horror Movie."

The New Jersey native also found himself in the headlines for his personal life in 2021 thanks to revelations he made in his autobiography, "You Can't Be Serious." From side hustles to stereotypical roles, here's a look at the untold truth of surely the only man to have worked with both the President of the United States and the parodists behind "Epic Movie."

You might have wondered how the star of "Harold and Kumar Go to White Castle" ended up landing a coveted role in the White House. Well, perhaps surprisingly, Kal Penn didn't rely on his high-profile connections. Not at first anyway.

During a 2021 appearance on podcast "Hello Monday," the actor revealed that despite spending 18 months working on Barack Obama's presidential campaign, he decided to apply for a job in his administration online instead of expressing an interest personally with any of his former colleagues. This modest approach didn't pay off, though. Indeed, it was only when Penn got talking to Michelle Obama at a function several months later that his political career began to take shape.

On hearing that Penn had refused to capitalize on his showbiz status, the First Lady brought her husband into the conversation where they both expressed a look "that unmistakably said, 'Are you really that stupid.'" Luckily, the Obamas were able to overlook Penn's lack of initiative and he was subsequently offered a Principal Associate Editor position at the White House's Office of Public Engagement. The actor acknowledged, "That was the first time that clicked with me, where I thought I was doing the right thing and not shaking things up and keeping my head down ... If I was serious about it, I should have made it known in a serious, professional way."

"Harold and Kumar Go to White Castle" grossed nearly $24 million on a rather modest $9 million budget, spawned two hit sequels and became the biggest buddy stoner comedy since the days of Cheech and Chong. But Kal Penn, who played Kumar in the franchise, initially believed that the world wasn't ready to see a second-generation Korean-American and Indian-American, respectively, take center stage in such a vehicle.

In a 2019 interview with NPR, the actor admitted that he took a lot of convincing from the film's creators Jon Hurwitz and Hayden Schlossberg in regards to its prospects: "They sent it to me — this was before it went out onto the market. And I called them and said 'This is amazing. This movie is incredible. You're never gonna sell it in Hollywood, because, trust me, nobody wants the brown and yellow guys as leads in the movie.'"

Penn was, of course, proved wrong. So much so, in fact, that he's still bombarded by Harold and Kumar obsessives, as he told GQ: "All these kids — I love them to death because they watch it like once a week — come up to me on the street and recite some totally obscene lines. I'm like, 'Oh my god! Why did that person say that? Why are they coming running towards me?' and then I remember, 'Oh yeah, it's something that I said.'"

In 2021, Kal Penn made headlines when he announced that he was gay and engaged to his boyfriend of 11 years who, in order to retain some privacy, he referred to simply as Josh. Speaking to Newsy shortly after, the "Van Wilder" star revealed that their early courtship wasn't exactly the height of romance. In fact, judging by their second date it's a surprise that they lasted another 11 days.

Penn recalled the particular Sunday afternoon at his home: "He rolls up with an 18-pack of Coors Light. And I had "Spongebob Squarepants" on the TV because I'm a romantic. He changes the channel, puts on the NASCAR race and then puts the rest of the beers in the fridge. And I was like, 'Did this just happen unironically?'"

The Hollywood star went on to explain that the sport had never been a particular favorite while growing up and that he saw this as a sign that the pair were entirely incompatible: "So I immediately was like, 'This obviously isn't going to work out.' He brought 18 beers, there are going to be 16 left that he can take with him." Luckily, Penn was eventually able to overlook Josh's passion for auto racing. In fact, he later became something of a convert himself, telling People, "Next thing you know, it's been a couple months and we're watching NASCAR every Sunday."

Like many Hollywood actors in the early stages of their career, Kal Penn was forced to take on various less starrier jobs in order to make ends meet. In fact, even after the success of "Harold and Kumar Go to White Castle," for which he walked away with the relatively paltry sum of just $22,500, the New Jersey native had to find work outside the world of showbiz to keep a roof over his head.

However, the fact Penn had become a semi-recognizable face often deterred employers from giving the star a temporary gig. In 2019, he told CNBC's Make It, "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? 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."

Luckily, Penn didn't have to worry about finding work elsewhere for too long. The former White House staffer certainly seems pleased he's permanently said goodbye to telemarketing ("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"). However, he does appear to miss the simpler days when he worked on a farm, and for one very superficial reason: he got absolutely "ripped."

How's this for unlikeliest celebrity interaction of 2021. While discussing his upcoming nuptials to boyfriend of 11 years Josh on Twitter, Kal Penn revealed that he once spotted Cardi B on a flight to Los Angeles. Although he didn't introduce himself at the time, he did end up dreaming about the "WAP" hitmaker while up in the sky, and specifically that she officiated at his wedding right there on the plane.

Cardi B ended up seeing this dream confession and subsequently did her best to turn this bizarre scenario into a reality, tweeting, "First, why didn't you say hi! Second, I'm licensed to do that sooo ... let me know." The rapper was no doubt only being polite but Penn seemed strangely into the idea.

Indeed, the "How I Met Your Mother" star then responded, "You're the best. Was gonna say 'Hi' but didn't want to be disrespectful (your do not disturb light was on). Let's do it! We're down if you're down!" Cardi B replied, "I'm down, I'll get my suit." Let's just hope the chart-topper is prepared for the "big-a**" wedding Penn and Josh are aiming for.

Students on the University of Pennsylvania's Asian-American Studies program in 2008 no doubt did a double take when they walked into one particular class. For the lecturer was the star of goofy stoner comedy "Harold and Kumar Go to White Castle." Thankfully, Kal Penn wasn't there to vouch for the merits of the Double Cheese Slider but to impart his words of wisdom on Hollywood.

Penn instructed two classes, "Contemporary American Teen Films" and "Images of Asian Americans in the Media," during his detour into education. And he soon won round even the most dubious of students, with one telling The Daily Pennsylvanian, "I was a little skeptical at first about what credentials gave him the right to teach a class at Penn. By the end of the class, I realized it wasn't his academic credentials that got him here, it was his experience in the field — which is equally valuable."

Penn obviously enjoyed the experience as six years later, he returned to his UCLA alma mater to teach a sociology course titled "Hope, Change, and Fist Bumps: Young Americans and The Obama Presidency." The actor, who arranged for his class to meet the POTUS himself on the LAX tarmac after an Air Force One flight, was again given the thumbs up. Student Jazmin Samano told the university's official site, "Coming into the class I expected it to be a learning experience. But now I'll have an experience to remember for the rest of my life."

In 2017, Kal Penn discovered a heap of old scripts that he'd once auditioned with as a fledgling actor and subsequently shared the most embarrassing on Twitter. Embarrassing for the Hollywood industry that is — for almost every single one he posted featured at least one blatant display of racial stereotyping.

Take the "King of Queens" audition, for example, in which his character's name Sanjib was made fun of. Or a show called "The Stones," which never made it past the pilot stage, that demanded Penn speak his dialogue in an accent. And then there's the scene in "Smart Guy" which didn't even bother to give the 'Foreign Student' the courtesy of a name. And rather depressingly, the list went on and on.

When asked by Vanity Fair which script he found the most offensive, Penn revealed that he couldn't choose just one: "That was so normal; these were the auditions that you would get. It was more of ... a slow-building disappointment or anger, as opposed to shock. And the reactions have been interesting. There are a number of other performers of color, and women, and folks with disabilities, and people who are 'overweight' who have replied to that tweet chain saying, 'Oh, that is exactly how it is right now for me.' What was surprising to me was how surprised people were."

You might expect that the man who both starred in the Harold and Kumar franchise and served in the Obama administration would be the perfect choice to host a comedic educational show titled "The Giant Beast That Is the Global Economy." "The Big Short" director Adam McKay and "Planet Money" podcaster Adam Davidson certainly thought so when they offered Kal Penn the gig in 2019. But it turns out that the actor was as clueless as his most famous stoner character.

Speaking to podcast "The Frame," Penn explained that his ignorance actually ended up working in his favor. Indeed, although they were initially surprised that the one-time White House staffer had little knowledge of fiscal policies, McKay and Davidson realized that their first choice still had plenty to offer: "I realized they were calling me stupid, which was fair. Basically they wanted a host whose lens would be the same lens of the audience."

Penn ended up exploring everything from blockchains and money laundering to counterfeiting and futures trading in the eight-part series, something he's proud to have been involved with: "It's nice to work on a show at a time where we're not questioning the validity of what we're looking at. We're just questioning our interaction with the material. How much agency do we have over these things? And how can we change the system for the better?"

In 2017, Kal Penn and all his colleagues on the President's Committee on Arts and Humanities decided to leave their posts en masse following the controversial "both sides" remarks Donald Trump made about the Charlottesville nationalist rally in which one woman lost her life. The "Clarice" actor posted the resignation letter on his Twitter account.

Penn later explained to CNN's Chris Cuomo (via EW) why the committee felt such a drastic step was necessary and why they didn't attempt to change the desperate situation from within the administration. He dubbed Trump a "tiny-fingered vulgarian who loves to tweet crazy things as his way of getting policy done," while also noting, "You have a White House that has gone into federal agencies and essentially put in a freeze. So they're wasting taxpayer dollars, the agencies are often not allowed to do anything at all."

The White House later claimed in an official statement that the committee's funding had already been withdrawn by Trump before the resignation, stating "In its current form it simply is not a responsible way to spend American tax dollars." However, Penn was soon quick to dismiss this as fake news, tweeting, "You can't break up with us after we broke up with you."

Turns out that Kal Penn has one of his co-stars on medical drama "House" to thank for his brief pivot into the political arena. Indeed, after becoming friends on the Fox hit, Olivia Wilde invited the actor to join her at a 2007 event supporting Barack Obama's presidential campaign.

Although Penn had read the future 44^th's memoir, he had little interest in becoming a member of his administration. In fact, he practically had to be guilt-tripped into attending the function by Wilde after she brought up the fact that his grandparents had marched with none other than Mahatma Gandhi.

However, the UCLA graduate experienced something of an epiphany when he eventually took up Wilde's offer of a plus one, as he told NPR: "So, I went to this event with her, really actually liked it ... [and] was enamored enough by his campaign. So [I decided to] do three days [of campaigning] in Iowa before the caucuses ... And then he won ... And there was an opportunity to serve in the White House, and ... you know, what are you gonna say, 'No, Mr. President, I have another stoner movie to make.'"

Kal Penn can still vividly recall the time he realized his destiny lay in the showbiz world. And a reimagining of Frank L. Baum's classic novel "The Wizard of Oz" was the catalyst. Speaking to CBS News in 2021, the "Sunnyside" star revealed how appearing as the Tin Man in a production of "The Wiz" staged by his New Jersey school completely changed his life.

Penn said, "It was just the first time I experienced being in the zone as an actor. I put the axe up and I turned to the audience and I say, 'All you fine ladies out there ...' and I just did this pelvic thrust, and the crowd went nuts! And I was just, like, that feeling was interesting." The star then tried to chase that same feeling in various other school plays before going on to study Film (and sociology) at UCLA and eventually land his first screen credit in the 1998 short "Express: Aisle to Glory."

And three decades on, Penn still gets that same thrill whenever he steps onto a set. He explained, "I really feel incredibly blessed when I have the chance to be part of a project that I'm really passionate about. For the same reason that I was passionate about 'The Wiz' in eighth grade, there's still an opportunity as an artist to just make somebody laugh or feel some happiness with other humans in another space and time."

Kal Penn is obviously a keen believer in paying it forward. After emerging victorious in the "MasterChef Celebrity Showdown" in 2017, the "Deadbeat" star gave away his prize money of $25,000 to the United Nations Relief and Works Agency for Palestine Refugees in the Near East. He later tweeted, "Much of our own media attention is focused away from the human stories of children and families who are suffering due to displacement against the rule of international law, terrorism and violence from so many sides. So having the chance to cook [for UNRWA USA] on MasterChef seemed like the right thing to do."

But Penn doesn't always have to beat Cheryl Hines in a taco-off to give things back. That very same month the New Jersey native responded to a racist tweet by setting up a crowdfunder dubbed "Donating To Syrian Refugees In The Name Of The Dude Who Said I Don't Belong In America."

The UCLA graduate ended up raising over $877,000, just a tad over his initial $2,500 target. Penn later tweeted he was left "speechless" by the generosity toward the campaign which he launched to "show the world that the American people care very much for everybody, especially refugees, contrary to what our current administration is trying to do in our names."

In 2013, Kal Penn came under fire for pledging his support to the stop-and-frisk policy in which New York police can search anyone for contraband, something which was deemed unconstitutional due to its targeting of the Latino and African-American community. But rather than doubling down on his viewpoint in response to the backlash, the "Battle Creek" actor refreshingly acknowledged that he shouldn't have entered the conversation.

Referring to the furore about his remarks, Penn told Salon, "I think, actually, that it was a very sobering eye-opener in not being quite so flippant in what you think might be a quick conversation. What a stupid mistake on my part, first of all. I obviously was not informed about this, frankly. Everything political that I tweet is something that I know enough about to comfortably have a well-informed position. This is the one example of an issue I didn't know enough about."

The actor went on to reveal that he'd been in contact with advocacy groups to learn more about the policy and why so many were upset about his championing of it. He concluded, "I think the phrase 'teachable moment' might be a little overused, but it really was a teachable moment for me. I certainly regretted tweeting that, and it's not what I feel. Lesson learned: If you're going to tweet something about politics, particularly after you've worked in politics, you need to be better informed about it."

Kal Penn once explained to CNBC's Make It that being a Hollywood star isn't always as lucrative as you might expect. "You deduct your taxes, 10% to your agent, 15% your manager, 5% to your lawyer, your publicity fees and then your rent," the "Designated Survivor" star grumbled while breaking down the rather miserable rules of the actor's pay check.

But Penn has obviously been shrewd with whatever money he has been able to keep for himself over the years. According to Celebrity Net Worth, he now has an impressive $10 million in the bank. And the one-time Obama aide isn't averse to splashing the cash, either. Per Variety, in 2008, he forked out a cool $1.2 million for a 1,600-square foot three-bedroom home in the star-studded neighborhood of Hollywood Hills, a property he sold for nearly $1.6 million just over a decade later.

Penn no doubt got paid handsomely for his brief stint in the White House Office of Public Engagement as the Principal Associate Editor. But the star is likely to have made the majority of his fortune thanks to his prolific work rate as an actor. Since making his screen debut in 1998 short film "Express: Aisle to Glory," Penn has racked up no fewer than 80 TV and movie credits.