In an email to an FBI agent during his background check when Kal Penn first joined the Obama White House as an associate director of the Office of Public Engagement in 2009, he made a joke so innocuous he can no longer remember it. The agent just responded, “OK.” Penn immediately replied to clarify he was kidding, he told me this week. “And she goes, ‘We do have a sense of humor, you know.’”“I’m like, OK, cool, I’m just not going to make any more jokes.” That approach won’t work in the job he’s gunning for these days. Penn told me about his federal faux pas shortly after taping his first show as a guest host of Comedy Central’s long-running fake news program, The Daily Show. It’s probably not fair to describe the job Penn is seeking as “permanent,” since nothing in this business is, but he is unabashedly campaigning to secure it beyond this week. He is the 8th guest host following Trevor Noah’s departure, one of only a couple to signal a real thirst for the job, and there are murmurings he is firmly in the network’s frame. But Comedy Central certainly won’t be giving him the job until they see that he can do it, which leaves him in the position of auditioning for it on air across four consecutive nights. “This week is going to be stressful,” he told his second guest on Monday night, Grover the Muppet. His first guest that night was a former… Click below to read the full story from Esquire
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