Conan O'Brien Explains Reason for His Divisive "Grease Ball" Hairstyle

Conan O'Brien Reacts to Criticism After Debuting New HairstyleConan O’Brien is always looking on the bright side. That’s why the comedian was able to make light of his polarizing hair transformation, explaining he was forced to ditch his pompadour style due to a painful sunburn he got June 18 at the grand opening celebration of former President Barack Obama’s presidential library in Chicago. “It’s three hours-plus, and when it’s over, I’m so glad that I put the sunblock on,” O’Brien explained on a behind-the-scenes clip of his Conan O’Brien Needs A Friend podcast obtained by Entertainment Weekly July 22, “and I’m feeling really good about myself. Like, smart move.” In fact, the former late night host felt even better when he ran into Stephen Colbert and David Letterman at the event, who he said looked like they had been “playing in a sandbox with plutonium—their faces are just bright, bright red.” However, O’Brien had to dismount his high horse after a while when he felt that something was amiss. “A day or two later, after the event, I feel like my skull is on fire,” he continued, “and then two days after that, my [scalp] is really itchy, and whenever I itch it, it looks like a snow globe. It looks like white freckled confetti is pouring off of my head. It’s disgusting.” Eventually, O’Brien realized that the top of his head had been “roasted” by the sun and needed to be treated. Paul Morigi/Getty Images; Team Coco/YouTube“Someone said to treat this, you’ve got to rub oil into it,” he shared. “So this morning, I rubbed oil into it, not thinking about the podcast when we went on camera, and then I come in and I look like I’m in [the band] Sha Na Na. I’m a grease ball. I’m so greasy.” Indeed, fans took notice of O’Brien’s slicked back hairstyle during the July 20 episode of his podcast, which was recorded less than two weeks after his visit to the presidential library opening. But as he put it in the clip, the oil was preventing his classic poofy hairdo because it was “weighing my hair down and my hair can’t do its normal thing.” Still, O’Brien had fun with his temporary appearance. “I look like I want to fight one of you in the parking lot by swinging a chain at you in 1952, or a little switchblade,” he quipped. “I really feel different. I just want to fight people on the street. I want to get a hot rod and drive it around. I want to get Rizzo pregnant, so that Rizzo has a bun in the oven. You know what I mean?” Lamenting that he’s learned his lesson to wear a hat in the future, O’Brien conceded, “I’m a grease ball now, and I’m just gonna keep rubbing oil into my head until my skull heals.” For more stars who have made notable transformations to their hair over the years, keep reading… Jamie McCarthy/Getty Images for Netflix; John Cena/XJohn CenaTwo weeks after attending the Little Brother premiere with a full head of brown hair, the WWE legend debuted a shaved look ahead of his second hair transplant. "Round 2 of [Follicular Unit Extraction] Treatment and this time I went all in for best possible results," he wrote on X June 29, 2026. "Thank you Ken Anderson and the staff at Anderson Center for Hair for accompanying me on this journey!"HBO/Disney/Chris Bartolucci John OliverThe Last Week Tonight host debuted jet-black hair for a guest role on ABC's long-running soap opera General Hospital.Raymond Hall/GC Images; Instagram/Carrie UnderwoodCarrie UnderwoodTrading in her signature golden locks, the country music star wrote on Instagram in August 2025, "Well, the last time I saw my natural hair color, I was probably about 12 years old, but I thought it might be time to give it a second chance."Jamie McCarthy/WireImage; Matt Baron/BEI/ShutterstockSebastian StanThe Marvel actor said goodbye to Bucky Barnes' signature long hair in April 2025, showing off a shaved head at the Los Angeles premiere of Thunderbolts*.Steve Granitz/FilmMagicTan FranceThe Queer Eye star had fans doing a double take when he ditched his signature gray hair for a dark brown 'do in April 2026. The fashion stylist noted at the time that the dramatic transformation was for a role and "not a midlife crisis."Sami Sheen/InstagramSami SheenThe daughter of Charlie Sheen and Denise Richards shared her at-home hair dying journey, including its many missteps, on TikTok and raved about the results. “I've been wanting to do this to my hair for years now," she said, "and I'm so happy that I finally did it.”Edward Berthelot/Getty Images / Taylor Hill/FilmMagicJessica ChastainThe Help star debuted her "choppity chop," she she put it, on the red carpet of the Breakthrough Prize Ceremony in April 2026. Shane Anthony Sinclair/Getty Images; Instagram/Jason MomoaJason MomoaIn July 2025, the actor shaved off his beard for the first time in six years to film Dune: Part Three, which required him to rock a clean shaven look to reprise his role of Duncan Idaho.Denise Truscello/Getty Images for Live Nation Las Vegas/Instagram/NBCKelly ClarksonThe American Idol winner debuted a shorter hairdo in a July 2025 The Voice promo, trading her signature blonde waves for a shorter, darker bob style.Instagram / Chris Pratt / Matt Baron/BEIChris PrattThe actor debuted a bearded look, which he sports on season two of The Terminal List, in June 2025.John Nacion/Variety via Getty Images; Jun Sato/WireImageFinn WolfhardThe Stranger Things star changed up his trademark shaggy hairstyle in May 2025 by debuting a buzzcut at the 2025 Crunchyroll Anime Awards in Tokyo, Japan.Jon Kopaloff/Getty Images; Steve Granitz/FilmMagicJoJo SiwaIn March 2025, the "Karma" singer debuted her rainbow mohawk at the GLAAD Media Awards. Instagram; TikTokEmily RatajkowskiIn a March 2025 TikTok video, the model called this 'do with shaggy bangs the "worst haircut of my life."Instagram / Gypsy Rose BlanchardGypsy Rose BlanchardThe Gypsy Rose: Life After Lockup star debuted a short bob in March 2025, more than two months after giving birth to her and fiancé Ken Urker's first child, daughter Aurora Urker.Clifton Prescod/Bravo/Charles SykesWhitney RoseThe formerly blond Real Housewives of Salt Lake City star debuted a red bob on Watch What Happens Live in January 2025.Instagram / Hailey BieberHailey BieberThe model debuted lighter locks in September 2024, a month after giving birth to her and Justin Bieber's first baby, son Jack Blues Bieber.Pascal Le Segretain/Getty Images/Araya Doheny/FilmMagicLily CollinsThe Emily in Paris star debuted her dramatic transformation at the world premiere of her new horror movie, MAXXXINE, in June 2024. "Changing my hair always brings out different sides of my personality and I love playing around," Lily told Vogue. "This cut and color feels bolder and yet somehow lighter. And completely more me—right now."Sean Zanni/WireImage/John Nacion/Variety via Getty ImagesKatie HolmesWhile attending Chanel's Tribeca Film Festival Artists dinner in June 2024, Katie debuted a subtle, yet striking transformation of rich caramel balayage highlights that were blended throughout her brunette tresses.Kylie Jenner / InstagramKylie JennerThe Kardashians star debuted a platinum blonde look and a bob haircut after rocking waist-length strands for quite some time. "Did someone say they missed king kylie," Kylie teased in the caption of her June 8 Instagram post, to which her sister Khloe Kardashian cheekily replied, "I did! I did!!!!!!"Gilbert Flores/Variety via Getty Images/Pierre Suu/Getty ImagesLisa RinnaThe former Bravo star debuted a platinum blonde look during 2024 Paris Fashion Week Haute Couture.Elisabetta Villa/Getty Images for Bulgari/Prodip Guha/Getty ImagesPriyanka ChopraThe Heads of State star debuted a drastic haircut—a shoulder-grazing bob—while attending a Bulgari event in Rome i May 2024. TikTok / Jessica BielJessica BielIn May 2024, the actress chopped her hair into a bob that many fans on social media said reminded them of one of the looks she sported as Mary Camden on the '90s series 7th Heaven.Instagram / Megan FoxMegan FoxThe Transformers actress returned to her dark brown tresses and debuted a sassy bob in May 2024, a month after she dyed her hair blue to enter what she dubbed her "Jedi era."Stephen J. Cohen/Getty ImagesDannielynn BirkheadAt age 17, the daughter of the late Anna Nicole Smith debuted a new lob hairstyle overnight during 2024 Kentucky Derby weekend, which she attended with dad Larry Birkhead.Emma McIntyre / Getty Images for Baby2Baby / Instagram / Demi LovatoDemi LovatoThe singer debuted a lighter, shorter 'do in April 2024.Kelly Osbourne/InstagramKelly OsbourneThe Fashion Police alum debuted a blonde bombshell hair transformation May 8.Vivien Killilea / Getty Images for Homeboy Industries / Chip Somodevilla / Getty ImagesKim KardashianBack to blonde: Kim debuted a new platinum 'do in April 2024.Michael Buckner/Variety via Getty Images/Neil Mockford/WireImageRihannaThe Fenty Beauty founder debuted a bright blonde hair transformation April 17 while celebrating her latest Fenty x Puma collection in London.Stefanie Keenan/Getty Images for FRAME/Michael Buckner/Variety via Getty ImagesDelilah Belle HamlinThe model debuted a bleach blonde pixie cut at the FRAME event April 4.Megan Fox/Instagram/Dimitris Giannetos/InstagramMegan FoxThe Jennifer's Body star traded in her bubblegum pink tresses for a baby blue bob, which she debuted April 2.For the latest breaking news updates, click here to download the E! 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