
Kal Penn's move from Hollywood to politics didn't initially go very smoothly.

The 45-year-old actor reveals a lot of life lessons in his recent biography, You Can’t Be Serious. But you might not want to take his advice on how to impress a future president.
Penn's book title encapsulates a lot of his story. The New Jersey native made his name in the zany "Harold & Kumar" comedies from the mid-2000s, but also proved more serious acting chops on the Fox hit medical drama, “House.”
LISTEN NOW: Kal Penn got 'schooled' by Barack Obama

It was a shift into politics soon after though that caused him to revert to some humorous situations, if unintentionally, as he talked about recently on the podcast, The New Abnormal.
Apparently, Penn was quite adept at embarrassing himself in front of Barack and Michelle Obama. In 2007, as Uproxx reported, he was invited by his “House” co-star, Olivia Wilde, to an event for the then-presidential candidate.
Kal used a moment to try to impress Obama with his knowledge about biofuels, paraphrasing an article he’d recently read.
”[Barack Obama] gave me that smirk and he goes, ‘Oh yeah, I read that article in Foreign Affairs too,’” Penn recalled. “If you had read my website carefully you would’ve seen that I’m proposing investing in corn-based ethanol as a bridge to cellulosic ethanol so that we can make fuel from things like our grass clippings and the leaves that we rake in our front yards. And he gives me another smirk and walks off, and Olivia is loving every f***ing minute of this. She’s like, ‘You just got schooled by Barack Obama.’”

Around that time, Penn had been planning a move into the political sphere, and had already applied for a DC job via change.gov, for which he never received a response.
Landing at another event not long after, he ran into future First Lady Michelle Obama, and the initial impression on her went about as well as it had on Barack.
“I told her I put my résumé on change.gov like the email said,” Penn explained, “and she looked at me like I was the biggest idiot in the whole world, and I realized probably how ridiculous it sounded. She was so weirded out by this she called the president-elect over… and then looks at me and says, ‘Tell him what you just told me.’"
“I said, ‘Well, sir, you know, I did apply for a job at the White House in case there was anything that I would be qualified doing,’” Penn continued. “And he looks at me and says, ‘Who did you apply with?’ And then I was like oh God, this again. I said ‘I applied on change.gov.’ And unlike his wife he smirked at me and it was the same idea though, the smirk was like, ‘God, you idiot’ and he said something like, ‘Why didn’t you reach out to anybody?’”
Apparently neither humiliating dress-down dented the Obama’s impression of Penn too much, as In 2009, he left acting to join the Obama White House as Principal Associate Editor in the White House Office of Public Engagement. He then became co-chair of Obama’s reelection campaign and was later appointed to the President’s Committee on the Arts and Humanities.
What was the lesson he learned from all that?
“My biggest takeaway from that experience was,” Penn concluded, “I’m a gigantic idiot.”
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