Conan O'Brien's comedy often revolves around his awkward self-deprecation. Conan harnessed his awkwardness and channeled it into a consistent bit that delighted his fans for 30 years. But sometimes, even a master of awkward harnessing like Conan can't keep things under control.
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Conan is incredibly skilled at pushing through even the most unintentionally awkward moments in his interviews, yet when it came to things like keeping his friend Norm MacDonald under control or getting one word out of director Abel Ferrera, this master interviewer was helpless. These are a few times when things got especially awkward for Conan, and spoiler alert; a lot of them do involve Norm Macdonald.
First on the list is one of the few cooking segments Conan did on his show after it had moved to TBS. Conan invited Giada De Laurentis who first taught Conan how to properly order food in Italian and then was going to teach Conan how to make chocolate linguini, which is actually spicy and savory and not a sweet dessert. However, Conan could not help but laugh when he realized his production team forgot to plug in the stove top they were supposed to use for the show. With a smile, Conan just said "This show is so dumb." and with Laurentis and Andy Richter they proceeded to demonstrate how to make the dish.
Another moment that got a little awkward for Conan was when he and his pal Norm Macdonald, were cooking a fish dish with Gordon Ramsay. A high-energy Ramsay took mild exception to when Norm called him a "cook" instead of a chef. But the moment was fleeting and Gordon carried on with the lesson. But when Norm said, "I'm not gonna eat this sh*t!" Conan lost it, much to the delight of the audience, while belting "WHY EVEN DO A COOKING SEGMENT!?" repeatedly and taking a giant swig of the cooking wine.
Garlin is currently caught up in a sexual harassment scandal but before that, he was a very well-liked comedy actor. However, fans were a little less enthusiastic when he wouldn't stop doing his bit and kept interrupting Conan's interview with Andy Daly. The comment section on that video when it was uploaded to YouTube shows many fans who wanted to hear about Daly's new project since he is a former sketch actor from Conan's NBC shows.
Conan could interview almost anyone, but considering how Conan is a Harvard-educated man with an immense knowledge of literature and history, having reality TV stars on just feels somehow out of place. Conan pushed through but it was difficult to find common ground with Snooki and JWoww. Also, pretty much out of nowhere, Conan brought up the topic of fake eyelashes, and Snooki and JWoww put some on him. The bit just didn't land the way others have, Snooki and JWoww just felt out of place.
Once again, Norm Macdonald made things a little uncomfortable for Conan, although fans online think this was one of the many reasons why Macdonald was one of the best late-night guests a host could have. Throughout the interview, Macdonald could not help but interrupt to point out how breathtakingly beautiful he thought Keke Palmer was. A flattered Palmer was left almost speechless. It was a sweet moment, though Conan still had to pick up the pieces thanks to Norm, once again.
One Reddit user called Bieber the "worst guest I've ever seen." Bieber was still young and had just blown up, and many were not excited about the high-pitched teen or his increasing antics. Conan pushed through as best he could, but there is only so much a Harvard-educated comedian and a teenage heartthrob can bond over. Conan made sure to conclude the interview by pelting Bieber with Peeps.
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While fans might have feelings about Snooki and Bieber's interviews, Conan is on record as saying that Abel Ferrara was the worst interview he ever had. Ferrara is visibly uncomfortable and fidgety and Conan, although he endures it, is visibly more frustrated than in any other interview. Also, Ferarra was so desperate to get out of the interview he tried to escape the building minutes before but was brought back by NBC staff.
It became a moment of comedy gold, and Scherzinger laughed it off, but Conan was, as the kids say, caught in 4k. While answering a question, Scherzinger told Conan to focus, and gestured to her face, indicating she had caught Conan looking at her cleavage. Scherzinger was wearing a very low-cut dress, to which Andy Richter pointed out that not expecting Conan to look just a little was "so unfair." Conan then wrapped up the incident with some of his classic physical comedy, as one can see in the clip.
While Conan's least favorite interview was with director Abel Fererra, fans online seem to think that his Late Night interview with Kari Wuher of MTV was his most awkward. Seriously, Google "Conan awkward interview" and that interview is one of the first to come up. Conan endures, as he is one to do, but Wuher seemed stand-offish and uninterested in his questions. She also didn't seem to get Conan's sense of humor.
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For the record, Smith looks back at this interview fondly, as do many Conan and Norm fans. Smith at the time was still doing Melrose Place and was promoting her movie with Carrot Top, Chairman of The Board. Norm interjected at every point he could with a joke or one of his famously (seemingly innocent) candid questions. "Wait are you talking about Melrose Place?" made Conan do a face palm, but the real winner was the ending joke about her movie with Carrot Top, "I bet the board is spelled "B-O-R-E-D." A delighted yet defeated Conan had to step away from his desk he was laughing so hard.