Comedian Katt Williams has built a reputation for bluntly speaking his mind, whether that’s onstage or in interviews. However, a recent story he shared in front of the first and only former Black first lady, Michelle Obama, has some fans floored. Williams, 54, was the latest guest on the Dec. 3 installment of Obama’s “IMO” podcast with her brother, college basketball coach-turned media personality Craig Robinson, 63. At one point during their chat, Williams shared his rags-to-riches story, recalling how he worked as a salesman before his comedy career took off. The Ohio native made a shocking revelation to Barack’s wife about how selling books, magazines, and cleaning products ultimately changed his life.  Stand-up comedian Katt Williams shared a wild story about his pre-fame days with former first lady Michelle Obama. (Photo by Olivia Wong/WireImage; Photo by Dia Dipasupil/Getty Images) ’All Lies Will Be Exposed’: 5 of the Boldest Predictions from Katt Williams’ Club Shay Shay Interview That We’re Still Waiting to Come True “I’m doing door-to-door sales when I knock on the door of five ladies of the night, and they are in a traumatic situation,” Williams told Obama and Robinson. Apparently, the women’s pimp was killed in front of them. Obama appeared shocked to hear about Williams’ prior run-in as she responded, “This is another like, ‘What!?’ I know everybody here is just like, ‘What!?’” “You were already dressed for it,” Obama quipped, noting Williams was wearing a blazer, black tie, and a fitted hat worn backward. Williams then joked that he later “volunteered for the pimp position.” The “Friday After Next” movie star went on to explain how his new female associates taught him how to run the world’s oldest profession. He also cites the experience as one that impacted his understanding of manhood. View this post on Instagram A post shared by Pinky Hall (@pinkyyumyum) “They taught me so much,” Williams said. “I wasn’t there very long, but those ladies, along with my sainted mother, those ladies really showed me what it was like to be a man. Because every night, for hours, they would just talk about everything wrong with men.” A clip of Williams’ conversation on “IMO” made it to social media, and commenters were stunned that the Primetime Emmy Award winner was honest about his past with the wife of former President Barack Obama. “Why would he say that in front of her?” one Threads user asked. “I love how he looked around before he said ‘ladies of the night’ like he wanted to make sure this was the most appropriate way to describe them in front of our First Lady,” another pointed out. Most were in shock that he would say such a thing, but many suspect Michelle’s reaction wasn’t that surprising. One who felt she knew what she would be getting with the “Wild ‘n Out” alum posted, “Michelle knows who Katt is.” Another on the platform read, “Talking pimpin’ [with] the Obamas is a feat that nobody can ever say they’ve done. Katt Williams really is in uncharted territory.” View this post on Instagram A post shared by IMO with Michelle Obama Craig Robinson (@imopodcasts) Someone replied, “Remember, they’re from Chicago, so they completely understand! They invited Katt Williams before many other comedians of his caliber! Katt Williams is one of the many GOATs!” Williams was able to transfer his pimp persona from his standups to the screen. He had a supporting role as Money Mike in 2002’s “Friday After Next” starring O’Shea “Ice Cube” Jackson Sr. and Mike Epps. “Regardless of what the role is, the first thing I do is erase me from it. So anything that I would naturally do, that’s what I’m not going to do, because I’m playing a different character,” Williams revealed in his now-infamous 2024 “Club Shay Shay” interview. He continued his breakdown of the Money Mike character by adding, “I then create this person based upon real-life circumstances. So I don’t have to wonder what a pimp thinks ’cause I’ve been in that position for a little while.” @cultureratedpv Today’s mantra: Don’t be sorry, be careful @icecube @therealmikeepps #FridayAfterNext #KattWilliams #MikeEpps #IceCube #Halloween #MoneyMike #CultureRated #PrimeVideo ♬ original sound – Culture Rated – Culture Rated The showbiz veteran also voiced A Pimp Named Slickback for a 2005 episode of “The Boondocks” animated sitcom. In 2006, Williams scored a breakout hit with the “Katt Williams: The Pimp Chronicles Pt. 1” special on HBO. “It’s Pimpin’ Pimpin’” followed in 2008 with “Pimpadelic” dropping the next year. His most recent special titled “Woke Foke” hit Netflix in 2024. He has since appeared in numerous movies and television shows over the last three-decade career and won an Emmy for Outstanding Guest Actor in a Comedy Series in 2018 for his performance in FX’s “Atlanta.” ‘Why Would He Say That In Front of Her?’: Katt Williams’ Pimp-Life Story About ‘Five Ladies of the Night’ with Michelle Obama Has Fans Covering Ears  ...read more read less