American talk show host Conan O’Brien started his career in comedy when he was at Harvard University where he was a writer for the university humor magazine named Harvard Lampoon. After his graduation, he started at HBO as a writer for the comedy series Not Necessarily the News, which was aired from 1983 to 1990.

Conan O’Brien is best known for hosting talk shows which he did for 28 years. In 1993, he took over David Letterman’s post as the host of Late Night, which he hosted for 16 years becoming the longest-serving host of the franchise. During an episode of Late Night with Conan O’Brien, the host revealed fans’ initial reaction to his underwear ad.

Conan O'Brien
Conan O’Brien on The Tonight Show

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Fans Did Not React Well to Conan O’Brien’s Underwear Ad

It is not uncommon for actors or celebrities, in general, to appear in different advertisements. While some celebrities have their own makeup or fashion brands to pose for, others do it for some other well-known brands. One of the things that celebrities are often asked to pose for is underwear. For instance, pop star Justin Bieber and actor Mark Wahlberg posed for Calvin Klein on two separate occasions.

Jennifer Love Hewitt
Jennifer Love Hewitt on Late Night with Conan O’Brien

Conan O’Brien was no less than a celebrity even in the 1990s, thanks to his reputation as an entertaining talk show host, specifically for hosting Late Show on which numerous Hollywood stars appeared. In 2006, during an interview with I Know What You Did Last Summer star Jennifer Love Hewitt on Late Night, O’Brien brought up the subject of underwear ads.

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During the interview, O’Brien revealed how the audience initially reacted when he said he was offered to pose for underwear. He said: “I get asked, all the time, please model our underwear.” The audience laughed at this and then went “Woo”. The talk show host-turned-podcaster then said: “You [the audience] initially laughed. I will never forget it and then you pretended, ‘Woo, s*xy’.”

Conan O’Brien’s mimicry of the audience’s reaction to his claim of being asked to do underwear ads only made the audience laugh more. Hopefully, the host was not too offended by how fans reacted.

Conan O’Brien Asked Jennifer Love Hewitt Inappropriate Questions One Too Many Times

Jennifer Love Hewitt Criminal Minds
Jennifer Love Hewitt in Criminal Minds

With time, people have become more aware of how inappropriate questions some talk show hosts can ask to their guests, especially the female ones. From Scarlett Johannson to Anne Hathaway, no actress has managed to escape the claws of these inappropriate questions about their looks or their body.

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Jennifer Love Hewitt was also a victim of this throughout the 1990s when she appeared on Conan O’Brien’s talk show to promote her upcoming project. More often than not, the host would find a way to make suggestive comments about her body or flirt with her and sometimes, go as far as asking questions about her love life.

During the interview in which they discuss the underwear ads, O’Brien asked her about the revealing clothes she was often seen wearing on the show Ghost Whisperer, which was aired from 2005 to 2010. Conan O’Brien was not the first person to do this kind of behaviour with Hewitt and he probably was not the last.

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