Rob Lowe’s Path to Dreamboat Status: Triumphs and Failures

Rob Lowe has become one of the most easily recognizable stars of our time. He is known for several memorable performances over the years and was even a member of the original “Brat Pack.” Rob Lowe has impressed us throughout the years with his talent and physical beauty.

Rob Lowe and Sheryl Berkoff / Amy Poehler, Rob Lowe, and Reshida Jones / Rob Lowe / Demi Moore and Rob Lowe
Source: Getty Images

Rob Lowe has been stealing hearts in Hollywood since he was a child and has barely aged a day in the process! Much like a fine wine, Rob Lowe’s talents and looks have only gotten better with age. This star has come a long way from his film debut in The Outsiders back in 1983 – and it seems that he’s not slowing down any time soon!

Fountain of Youth

Even though he got his start in a more serious film, The Outsiders, Rob Lowe was always seen as a “pretty boy.” It’s hard to escape that image when he’s been blessed by the fountain of youth in a way that no one else has, Hollywood royalty included.

Rob Lowe attends the 59th Monte Carlo TV Festival.
Photo by Stephane Cardinale – Corbis/Corbis/Getty Images

He started as a high school student with dreams of making it big in entertainment and ended up going on and working with many of his classmates throughout his career. But he quickly found himself at the center of a controversial scandal that could have jeopardized his entire career.

Early Childhood

The star was born Robert Hepler Lowe to his parents on March 17th, 1964, in Charlottesville, Virginia. His mother, Barbara, was a schoolteacher, and his father, Chuck, was a trial lawyer. His father must have been excited to see his later role in The West Wing as a character who followed in a path like his.

Rob Lowe as a toddler, sits in an oversized chair.
Source: Pinterest

Lowe’s parents decided that they would call it quits on their marriage. They divorced when Rob and his younger brother, Chad, were young. Their mother had gone through a couple of divorces and reportedly followed a new man to California and took her sons along for the ride.

Uprooted Lowes

Their mother moved them to bright and beautiful California. It was there that Lowe was able to connect with his passion for the stage while meeting people who would eventually become his colleagues. Had his mother not followed her new husband to Los Angeles, would he have become an actor?

Rob Lowe with his mother Barbara and siblings Chad and Micah.
Source: Reddit

It was in Los Angeles that Lowe kickstarted his career in Hollywood. He had classmates who were well-connected, and maybe they even helped him get to where he is now. Lowe can almost certainly thank his family’s relocation to the West Coast for his rise to success in the industry!

Classmates to Colleagues

Rob graduated from Santa Monica High School in 1982. He was one of many notable alumni, especially at the time that he was in attendance, including entertainers like Charlie Sheen, Sean Penn, Emilio Estevez, and Robert Downey Jr. Do you think any of them knew how successful they would become?

Rob Lowe, Tom Cruise, and Emilio Estevez at a premiere.
Photo by Frank Edwards/Fotos International/Getty Images

It was here at Santa Monica High School that Lowe honed his skills and passion for performing. He began acting in school and landed his breakthrough career role when he was just a year out of high school. He was cast in The Outsiders in 1983 and found his classmate Emilio Estevez to be his new co-star!

His Breakout Role

Lowe’s first-ever professional acting role was as Sodapop Curtis in Francis Ford Coppola’s famous film, The Outsiders. This movie was a film adaptation of the world-renowned novel written by S.E. Hinton. Not only did Lowe get to kick off his career with one of the greatest directors of all time, but he would also be ushered into the “adult” world!

Tom Cruise, Rob Lowe, C. Thomas Howell, Ralph Macchio, Matt Dillon, Emilio Estevez and Patrick Swayze on the set of The Outsiders.
Photo by Nancy Moran/Sygma/Getty Images

Lowe turned 18 while filming The Outsiders. Now, he was both a working actor in an iconic movie and an adult in the eyes of the law. His time as Sodapop would introduce him to other actors who would become his co-workers in the future, like Tom Cruise.

Welcome to the Brat Pack

It would not take long for his role in The Outsiders to turn into so much more. Lowe would soon be associated with a group of young, beautiful actors and actresses who would be known as “the Brat Pack.” They often appeared in a series of teen-centered coming-of-age films together in the 1980s.

Emilio Estevez, Demi Moore, Rob Lowe, and Melissa Gilbert at the Woodley Park in Van Nuys.
Photo by Jim Smeal/Ron Galella Collection/Getty Images

Other entertainers who were part of this group included Emilio Estevez, Demi Moore, and Molly Ringwald. These few actors would find themselves starring in notable films of the era, like Sixteen Candles, The Breakfast Club, and St. Elmo’s Fire – another that Lowe would later be known for.

St. Elmo’s Fire

Of all “Brat Pack” films, Lowe liked the one he starred in the least. Lowe starred in St. Elmo’s Fire, directed by Joel Schumacher. The film did not get the five-star reviews by critics they initially hoped for, but that did not stop the film from taking off and becoming a cult classic.

Rob Lowe, Ally Sheedy, Demi Moore, Emilio Estevez, Mare Winningham, Judd Nelson, and Andrew McCarthy on the set of St Elmo’s Fire.
Photo by Silver Screen Collection/Getty Images

The film is centered around a group of friends who recently graduated from Georgetown University. They were struggling with the realities of becoming adults, which resonated with their audience, and it became an instant hit. However, Lowe was not a massive fan of the film ; he liked other “Brat Pack” movies far more!

Lowe’s Favorite “Brat Pack” Films

Lowe has previously mentioned that even though St. Elmo’s Fire helped him gain teen idol status, it was not his favorite of the “Brat Pack” films. He has been quoted saying that, “My favorite film of the Brat Pack I’m actually not in, and that’s The Breakfast Club. I think The Breakfast Club and Fast Times at Ridgemont High are amazing.”

Judd Nelson, Ally Sheedy, Emilio Estevez, Molly Ringwald, and Anthony Michael Hall in The Breakfast Club.
Source: / Copyright: Universal Pictures

Lowe continued to reflect on his favorite movies from the group. “I’m very partial to About Last Night. St. Elmo’s Fire is its own animal, and there are people who you think would know better than to quote every line of St. Elmo’s Fire. Like Gwyneth Paltrow knows every line.”

He’s Deaf in One Ear

Did you know that Lowe is deaf in one ear? When he was just a baby, he survived a viral infection he caught at just eight months old. This viral infection was an undiagnosed case of the mumps, which frequently causes hearing loss by damaging the cochlea, an inner-ear organ that helps us hear.

Rob Lowe circa 1982 in New York City.
Photo by Robin Platzer/Images/Getty Images

This is a little-known fact about the star. He often finds it hard to be in loud, crowded places. As a result, he is not a huge fan of busy restaurants, which are typically very noisy. Since he has been dealing with this from a young age, he has learned the best ways to deal with it and move forward.

How Old Is Rob Lowe?

In 2021, Lowe is 57 years old, though he could certainly still pass as young and beautiful. He has managed to remain as youthful as he was when he started at just 17 years old. These days, he has moved on from his roles as teenage eye-candy to the token on-screen father figure.

Rob Lowe is flashing a shy smile while he visits
Photo by Noel Vasquez/Getty Images

After scandals like his sex tape, one of the first commercially released of its kind, in which he engaged in intimate activities with girls who ended up still being teenagers at the time, it’s unquestionably correct for him to have moved on from that blunder and grown into a new, more respectable man.

Teen Sensation

Lowe became known as a young and handsome actor in Hollywood, often earning himself the title “teen heartthrob.” He was known for his “pretty face” and iconic, deep blue eyes. It isn’t hard to see how he became one of the best-known teen idols of his time.

Rob Lowe is photographed on a balcony.
Photo by Paul Harris/Getty Images

Rob Lowe was hot by more than just association. Many other “Brat Pack” members were probably seen as more attractive than they were, if for no other reason than just having that group association. Lowe knew how gorgeous everyone thought he was and even admitted that the flattery often went to his head.

His First Playboy Mansion Visit

When Lowe was only 19 years old, Hugh Hefner had his representatives reach out to Lowe and invite him to a party at the epic Playboy Mansion. He initially attended the party with plans to meet up with one of the beautiful women who inhabited the mansion, but he was disappointed.

Rob Lowe is wearing a white t-shirt beneath a dark blue Levis denim jacket.
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

Lowe realized that the Playmate he planned to meet with was involved with a famous football player at the time. Lowe knew better than to get involved with her. He was disappointed, but he probably still managed to find company with the other available women!

Scandals Arise

Lowe managed to become a big star at quite a young age. Anyone who finds themselves at the center of attention while working their way into adult society might find themselves at the center of a scandal. Little did Rob know, but he was soon to fall into that category.

A photo of Rob Lowe.
Photo by Barry King/WireImage/Getty Images

Just five years into his career, Rob Lowe had to deal with a scandal that would nearly destroy everything he had worked for. In 1988, he went out to a nightclub and met some girls he later took back to his hotel room. They engaged in some intimate activities, and Lowe quickly learned something chilling… they were underage!

He Engaged With Underage Girls

Lowe reportedly had no idea that the girls he engaged in those activities with were underage. The young women said they were 21 years old, and maybe they looked the part – but, in fact, they were barely 16 years old. That is only the beginning of the brutal battle ahead.

A still of Rob Lowe from an old film camera.
Source: Reddit

Lowe and the girls made a sex tape of their night together. This was back in the days of VHS, which meant that once it got into the wrong hands, it could be copied and sold without consent. That is precisely the situation that Lowe and his underage partners found themselves in.

When “Going Viral” Meant Something Different

Rob Lowe was only 24 years old when this scandal nearly ruined his life. Though he was able to later joke about it, it still put him through his fair share of heartache. Celebrities at the time were often threatened to be exposed for what they did in the most intimate parts of their lives.

Rob Lowe speaks on stage in front of a crowd.
Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

When Lowe’s adult film (with minors!) was exposed, a tycoon of the adult film world managed to snag a copy of the tape. Al Goldstein got a hold of the video and soon managed to sell it to anyone with 30 bucks to their name. This was back when “going viral” meant something different!

Legal Problems Arose

Naturally, engaging in sexual activities with minors came with consequences (as it should)! After the girls he spent the night with took the tape (and subsequently released it), one of their mothers turned around and filed a lawsuit against the movie star. He blamed drinking for his poor judgment at the time.

Rob Lowe attends the
Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

Naturally, Lowe did not want to deal with this scandal any further. He settled out of court with the girl and her family, though the damage to his career was far from over. You’d think that he would have learned to shut his mouth afterward, but instead, he later admitted that he believed “[he] should have tried to make some money off of the tape!” Have you learned nothing, Rob?

Fans Turned on Him

When word got out about this controversial tape, so many of his fans turned on him. Lowe was heading downhill, and he was going there fast. The love and affection he used to get from his fans started to diminish, as fans believed they could see him as he was: a creep with a penchant for younger girls.

Rob Lowe at Limelight.
hoto by Patrick McMullan/Patrick McMullan/Getty Images

He was no longer getting the positive attention he was used to, and mainstream movie roles were suddenly not available to him. To make matters worse, Lowe was coping with these stresses in addition to excessive alcohol abuse, which would soon catch up with him.

Turning Lemons Into Lemonade

Everyone deals with their traumas differently. Lowe dealt with his letdown through substance abuse but was later able to get help and pull himself together. He finally made a joke about what happened to him when he hosted Saturday Night Live in 1990.

Nikki Glaser, honoree Rob Lowe and actor Ralph Macchio onstage at The Comedy Central Roast of Rob Lowe
Photo by Alberto E. Rodriguez/Getty Images

Through the years, other stars have taken digs at his indiscretions. During the Comedy Central Roast of Rob Lowe, comedian Nikki Glaser made some comments at his expense. “Rob defies age… restrictions. You’re an Adonis; look at you. I mean, you look sculpted; you put the statue in statutory rape. I had such a crush on you as a little girl; if only I’d known that’s when I had my best shot!”

He Dated a Princess

After spending a period of time in the shadows, hiding from the mess he had made for himself, Rob Lowe found himself dating royalty… literally! He spent some time dating Princess Stephanie of Monaco. When he was 22 years old, he flew to France to promote a film, where he met the princess herself.

Rob Lowe and Princess Stephanie arrive at an event.
Source: Pinterest

Dating Grace Kelly’s daughter came with its own kind of drama. Their romance was short, and as he divulged in his second memoir, it was a “whirlwind romance.” He said that he could not keep up with her games, so I guess he just was not destined to become royalty himself.

Return to the Big Screen

Lowe’s talent was apparent, but his questionable choices in the past compromised that. One of his first returns to the big screen was in the hilarious Mike Myer’s project, Wayne’s World. Though he was not a vital role in the film, it helped revive his career and put him back on the map.

Dana Carvey, Rob Lowe and Mike Myers in a still from Wayne’s World.
Source: / Copyright: Paramount Pictures

The 1992 film came out only four years after his sex-tape scandal and might have been the saving grace that kept him relevant in Hollywood. He used this as an opportunity to rebrand as a comedy actor, which is how many of today’s younger fans know him.

Siblings in Hollywood

Many people in Hollywood seem to climb the social ladder when someone in their family makes it big. I mean, look at the children of celebrities – they often get hundreds of thousands of followers on social media for nothing more than being related to someone famous! Rob Lowe’s brother, Chad, doesn’t exactly fit this description… but he kind of does!

Rob and Chad Lowe ride the
Photo by Mathew Imaging/FilmMagic/Getty Images

Rob’s younger brother Chad may not have made it nearly as big as his big brother, but he certainly did well for himself. He won an Emmy for his supporting role in Life Goes On, about a young man living with HIV. He also had recurring roles on ER and Melrose Place and was married to Academy Award winner Hilary Swank before their divorce in 2007.

He Has Dated Some Other Big Names

Rob Lowe has been around the block a few times, to say the least. His loyalty was continually challenged when he found himself surrounded by the temptation of the many beautiful women he interacted with on set. He has dated other celebrities, but can you guess which ones?

Rob Lowe and Winona Ryder attend the 45th Annual Golden Globe Awards.
Photo by Ron Galella/Ron Galella Collection/Getty Images

Some of the many women Lowe has added as notches on his bedpost include Fawn Hall (of the Iran-Contra scandal), Marlee Matlin, and Winona Ryder. He’s also dated Cornelia Guest, a debutante of the era. There were constant rumors that he was cheating on his girlfriend with every leading lady he crossed paths with.

His Relationship With Melissa Gilbert Was Turbulent

Melissa Gilbert is an actress who rose to fame after her role on Little House on the Prairie. Gilbert and Lowe were in a serious relationship for seven years, beginning when she was only 17 years old. This was Lowe’s longest relationship prior to meeting his wife, and it came with its own set of problems.

Rob Lowe and Melissa Gilbert attend an event.
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

Sure, they had been through some of life’s most significant battles together, but they also appeared to be as happy as they could be during their many red-carpet appearances. Their relationship withstood so much that Lowe had even proposed to her in 1996. They were engaged for a period of time before calling it off, reportedly after Gilbert suffered a miscarriage.

The Drama Doesn’t End There

Though there were many struggles this couple dealt with, one consistent problem with “pretty boy Lowe” was constant infidelity. She wasn’t necessarily a victim, though – Gilbert found her own ways to retaliate. One instance of Lowe’s cheating caught up to him when Gilbert got a sidepiece of her own.

Melissa Gilbert and Rob Lowe at a party.
Photo by Ron Galella/Ron Galella Collection/Getty Images

To be fair, despite being a strong, successful Hollywood couple, it seems that they practically walked into infidelity. For one of his Brat Pack projects, About Last Night, Lowe recommended his real-life girlfriend for the part. Unfortunately, his director told Gilbert that he went with Demi Moore instead because they “looked so good together.” Ouch!

He Hooked Up With His Co-Star

Not a single soul was shocked to learn that Lowe and his co-star, Demi Moore, hooked up while working together on About Last Night. This was definitely not his first affair, and even she recalled that she barely remembered their night together as she was abusing substances at the time.

Rob Lowe and Demi Moore in a scene from About Last Night…
Source: / Copyright: TriStar Pictures

After learning about her boyfriend’s steamy night with Demi Moore, she knew that revenge was her best method of retaliation. She was unfortunately stuck in the middle of nowhere, somewhere in Texas, making a movie about horses. She wasn’t into her co-stars, so she went on to have a steamy night with the third assistant director.

Not Their First Rodeo

Rob Lowe reportedly stole women from their prominent rockstar boyfriends, one of whom was Natassja Kinski. She was dating Duran Duran singer John Taylor at the time and seemed to love the game the two were playing. It seemed like a sport, and Lowe and Kinski were the only players in the game.

Rob Lowe and Natassja Kinski on the set of The Hotel New Hampshire.
Source: / Copyright: Orion Pictures

Kinski was a European model who was barely older than Lowe. The two were co-stars in the film Hotel New Hampshire, and things became heated between the pair. One evening while filming, Lowe’s girlfriend, Gilbert, called the hotel to check in on him. The operator shared some devastating news – he was in Kinski’s room!

What Happened Next?

Naturally, Melissa Gilbert was not happy. She got on the next plane to see him and confronted him on set. When arriving at the cast’s accommodations, Lowe could not give his girlfriend even the slightest excuse. The two were in for a long night of working out their relationship woes!

Rob Lowe and Melissa Gilbert attend an event.
Photo by Vinnie Zuffante/Michael Ochs Archives/Getty Images

After confronting her boyfriend, the two had a long night ahead of them. They reportedly spent the next “15 hours of crying, screaming, talking, making love, carrying on, and laughing.” There were many signs that this relationship was not meant to last forever, but kudos to them for trying to work things out!

Why Did Rob Lowe Leave The West Wing?

For years, Lowe was a supporting actor on the famous political drama series, The West Wing. This Emmy-winning series went on air in 1999, and the world has never been the same since! However, it seemed that he was ready to move on a little sooner than the show was.

Rob Lowe stars in NBC's
Source: Getty Images

No surprise, the rich always want to remain that way. Though the actor said that there didn’t seem to be a place left for his character, Sam Seaborn, sources close to the star, said that they knew it was about money. Lowe was earning more than $70,000 per episode but was upset to learn that Martin Sheen was making almost four times more!

He Met the Love of His Life

After years of dating a series of famous women (and those who weren’t as renown), Lowe finally met his forever match. He fell in love with Sheryl Berkoff, an ex-girlfriend of another Brat Pack member, Emilio Estevez. Berkoff and Lowe were set up on a blind date a few years earlier, but at the time, the spark was not there.

Rob Lowe and Sheryl Berkoff during
Photo by Ron Galella/Ron Galella Collection/Getty Images

As fate would have it, Berkoff was hired as a makeup artist for Lowe’s 1989 film, Bad Influence. The spark between them was now evident, and they instantly became the couple of the year. They overcame many of life’s battles together and would soon grow into adults who faced their problems head-on.

“She Made Me Examine How I Was Living My Life”

The two matured together as best they could. They struggled through the typical bits that couples do, and he later opened up about how he could have been better to her. “I had met my now wife, Sheryl, and was attempting my first try at monogamy—which was not really in my nature at the time—and I wasn’t able to do it.”

Rob Lowe and wife Sheryl Berkoff attend the 'True Lies' Westwood Premiere.
Photo by Ron Davis/Getty Images

The two managed to work through their struggles and came out stronger on the other side. She would not let him get off too quickly, and she actually demanded that he check into rehab. He was later quoted saying that this relationship “made me examine how I was living my life. That led me to get sober, which led me to change my life—giving me everything I now have.”

He Found His Forever Woman

“I found the right woman — my wife, Sheryl. And I knew if I ever was going to make it work, I had to get my act together… There’s no secret… You just have to be willing to work when it gets tough, and it’s going to get tough. It’s like having a career,” he said.

Rob Lowe and wife Sheryl Berkoff attend the closing ceremony of the 59th Monte Carlo TV Festival.
Photo by Arnold Jerocki/WireImage/Getty Images

Lowe continued, “when you have a long career, you’re going to have times when you’re not the ‘it’ guy. And it’s the same with love. There are days when you’re so into it, and there are other days when you were like, ehhhhh! The totality of time there’s going to be more days when you’re just so in love.”

He Became a Family Man

Through all the chaos Lowe found in his life, he finally hung up his party boy lifestyle. Something indisputable is his commitment to his family. He married Sheryl, and the two became parents to two lovely sons, Matthew and Jon Owen. He is so dedicated to being a dad that it was hard to watch them grow up.

Rob Lowe, Sheryl Berkoff, and their kids during
Photo by SGranitz/WireImage/Getty Images

Lowe admitted that on the night his first son headed off to college, he could not stop crying! He even went as far as to sleep in his son’s bed his first night away because he missed him so much. The family went on to have a reality show together, entitled “The Lowe Files.”

Pretty People Have It So Hard!

Many if not all people know him as the actor with “the good looks.” Granted, that could be almost anyone who has managed to strike gold in Hollywood, but in this case, it’s clearly Lowe at the center of attention! Unfortunately, he thinks he’s had it a little tougher… just because he’s so attractive!

Rob Lowe visits Hallmark Channel's
Photo by Paul Archuleta/Getty Images

He once reported that he felt there was an “unbelievable bias and prejudice against good-looking people.” The star continued in his memoir stating, “I often find, to my disappointment, that when the folks in the executive suites are paying for Rob Lowe, they want me to look like Rob Lowe, regardless of who I’m playing.” Well, that’s just… wow.

He Was Almost McDreamy

There are so many reasons why actors or turn down roles. Many come back later and say that they regret missing out, but when it comes to a part he turned down in Grey’s Anatomy, he has had very few regrets. Lowe turned down the role of Dr. Derek Shepherd, otherwise known as “McDreamy”!

Patrick Dempsey, as Derek Sheperd in Grey’s Anatomy.
Source: / Copyright: ABC

Seeing him in the role as the token “hot doctor” certainly wasn’t the most shocking. Later, he admitted that he was happy with who they ended up casting. “I agreed to meet with the people making Grey’s Anatomy. I had read it and loved it—the writing was crisp, real, and very entertaining—and it’s always been a good idea to hear out talented people.”

His Parks and Recreation Days

Rob Lowe joined the cast of NBC’s Parks and Recreation around the same time that he left ABC’s drama series, Brother & Sisters. During the second season, Rob Lowe made his Parks and Recreation debut, leaving his fans and co-stars obsessed with Pawnee’s newest addition, Christ Traeger.

my Poehler, Rob Lowe and Rashida Jones attend the
Photo by Michael Tran/FilmMagic/Getty Images

Lowe joined the show with his on-screen audit partner, Adam Scott, who played Ben Wyatt. Lowe played a happy and enthusiastic man who came in to hack up the city’s budget and walked into a community dynamic his character never expected. Chris Traeger would soon become a key player in the NBC series.

He Played Chris Traeger

Lowe’s character on Parks and Recreation was Chris Traeger, a state auditor who came in to hack up the fictional city of Pawnee’s budget. He was a fitness buff who looked at everything as a glass-half-full situation and was constantly looking for reasons to be happy.

Rob Lowe and Aubrey Plaza in a still from Parks and Recreation.
Source: / Copyright: NBC

His character came onto the show anticipating staying for a short period of time; in fact, he even kept his apartment back in Indianapolis because he didn’t plan to stay there long enough to get comfortable. However, as fate would have it, he would find himself crossing paths with characters who would change his life forever.

Chris and Ann

One of these many people Chris crossed paths with was Ann Perkins (played by Rashida Jones), Leslie Knope’s best friend and sidekick (played by Amy Poehler) . The two kissed at a party when Ann was drunk, not long after Chris arrived in Pawnee. It was instant attraction, but not always smooth sailing.

Adam Scott, Reshida Jones, Rob Lowe, and Amy Poehler in a still from Parks and Recreation.
Source: / Copyright: NBC

Ann resisted Chris for a while, and when they finally went out, Leslie and Ben (played by Adam Scott) both crashed the date for their own reasons. After all the drama was said and done, the two began a relationship – only to end up breaking up. Of course, their paths crossed again later on.

Ending His Parks and Recreation Stint

Lowe started as a guest star who used his household name to help the show get some more publicity and attention. He enjoyed his time so much that he voluntarily returned for more. By the third season, just after Chris Traeger was introduced as a cast member, the show became what we know it as today.

Rob Lowe and Reshida Jones in an episode of Parks and Recreation.
Source: / Copyright: NBC

Leaving Parks and Recreation came a bit naturally, as his role was always more conditional than others. He left because he felt there was nothing left for his part, that he had outlived his Parks and Recreation time. Since he chose to stay longer than they needed him, his role was expanded to suit him.

The Roast of Rob Lowe

Comedy Central has been hosting “roasts” of celebrities since August 2003. Comedy Central began producing televised versions of the annual roasts of the New York Friars Club, which have been occurring since 1950. Some of the guests of honor have included Hugh Hefner, Rob Reiner, and Chevy Chase.

Rob Lowe is laughing onstage during The Comedy Central Roast of Rob Lowe.
Photo by Alberto E. Rodriguez/Getty Images

When the show became what it is today, many A-list celebrities got on stage to laugh (and cringe) along with other stars. Rob Lowe was lucky to find himself at the center and had guest roasters including Jewel, Ann Coulter (what?!), Pete Davidson, Nikki Glaser, and Ralph Macchio.

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