Sarcastic Facts About Matthew Perry, The Flawed Friend

August 9, 2023 | Byron Fast

Sarcastic Facts About Matthew Perry, The Flawed Friend

If Matthew Perry’s Chandler was the one on Friends who made you laugh the hardest, his real-life story may have you reaching for a box of tissues. It seems that the laughs stopped as soon as Perry left the set.

The reality was that the off-camera Perry was facing multiple addictions, multiple heartaches, and the kind of loneliness that only a superstar can experience.

Not feeling sorry for the Emmy award-winning, multimillionaire yet? Just you wait... 

1. He Looked For Stability 

Matthew Perry was born in Williamstown, Massachusetts. Dad was actor and singer John Bennet Perry, and mom was Suzanne Langford. Langford was Canadian and worked for the Prime Minister at the time, Pierre Trudeau. 

Young Matthew Perry was looking for stability in his life. Sadly, it wouldn’t come from his parents. 

matthew perry

2. They Called It Quits

Dad was a familiar face to the public. He was, after all, the handsome sailor in the Old Spice aftershave commercials. Dad wasn’t, however, a particularly familiar face to Perry. 

You see, before Perry had his first birthday, his parents decided to end their marriage. This meant that Perry had to move up to Canada with his mother, so she could continue her career there. 

Dad wasn’t a real sailor, but Perry must have felt that he’d lost his dad at sea. 

Matthew Perry looking at camera with surprised face - 2012Kathy Hutchins , Shutterstock

3. He Fought

Up in Canada, Perry attended a rather prestigious public school called Rockcliffe Park. Two Dutch princesses had once attended there, and while Perry was a student he met up with his mom’s boss’s son. 

The story goes that Perry got into a fight with the Prime Minister’s son and beat him up. Incidentally, that young man grew up to be Canada’s current Prime Minister Justin Trudeau

Perry’s dream, however, wasn’t about throttling future politicians. He wanted to be a star. 

Justin Trudeau wearing blue suit with red tie ,looking at side - 2018MSC / MCI, CC BY 3.0 DE, Wikimedia Commons

4. He Was On A Quest

Perry knew he wanted to be in show business, so at the tender age of 15 he moved to Los Angeles. While there, he did manage to finish high school, but at the same time he was pursuing his dream of being on TV.

 After trying his hand at improv comedy, Perry landed his first big role. But he was about to learn a hard lesson.

 The show was a sitcom called Second Chance and believe me—it needed one. 

Screenshot: Matthew Perry looking surprised - from The Whole Nine Yards (2000)Franchise Pictures, The Whole Nine Yards (2000)

5. He Didn’t Get A Second Chance 

Perry's first significant TV role was on a show that didn’t quite know what it was. It started out as the supernatural Second Chance and then morphed into the more reality based Boys Will Be Boys

Ironically, the rebooted show didn’t get the second chance that its first incarnation promised: They canceled it after just one season. 

Perry took the cancellation hard, but he was no quitter. He wasn’t going to leave LA until he was a star. 

Screenshot: Matthew Perry wearing black suit and smiling - from Boys Will Be Boys (1987-88)20Th Century Fox Television , Boys Will Be Boys (1987-88)

6. He Was Sure This Was It

Next, Perry made a leap from the small screen to the large. The film was A Night In the Life of Jimmy Reardon with the soon to be famous River Phoenix

Perry was completely convinced that this was the vehicle that would make him—and his co-stars—famous. He even walked around  the set asking what they would all do once this film had made them all recognizable actors. 

Sadly, Perry was in for a rude awakening. 

Screenshot: Matthew Perry looking surprised - from A Night In The Life Of Jimmy Reardon (1988)Island Records , A Night In The Life Of Jimmy Reardon (1988)

7. He Was Forgotten 

The problem with A Night In the Life of Jimmy Reardon was that it suffered from a split personality. The people making the film wanted an adult comedy drama, and the suits at the studio wanted a teen movie. 

In the end, nobody got what they wanted. The film—and Perry—were both quickly forgotten. That’s two false starts for Perry. Was it time to call it quits? 

Screenshot: Matthew Perry is looking sad  - from Numb (2007)Fries Film Group , Numb (2007)

8. It Was A Very Special Episode 

By the late 1980s the TV sitcom Growing Pains was already a huge hit. Perry got an offer to join the cast for a limited run. In his episodes he plays Sandy, a boyfriend of the family’s daughter Carol. But this role couldn't have been darker.

This ended up being one of those emotional “very special” episodes that were famous at the time. Instead of providing tons of laughs, Perry’s Sandy crashes his car while inebriated and loses his life. 

This role on Growing Pains provides some eerie omens of what was yet to come for Perry. 

Screenshot: Matthew Perry is smiling and walking next to woman - from Growing Pains (1985-92)Warner Bros. Television ,Growing Pains (1985-92)

9. It Was Ominous 

There were a couple of weird coincidences about Perry’s time on Growing Pains. First of all, his final episode had the title "Second Chance," which was also the title of his failed sitcom. 

Secondly, one of Perry’s character’s traits is that he makes jokes when he is uncomfortable, which also sounds a lot like Chandler. 

The last coincidence is more ominous. Perry would go on to have a very difficult relationship with drink—just like his character Sandy. 

With these menacing clouds above, Perry went on to his next role. 

Screenshot: Matthew Perry looking surprised at camera - from Numb (2007)Fries Film Group , Numb (2007)

10. He Failed To Help 

After literally dying on Growing Pains, Perry went on to become a cast regular on another sitcom. CBS's Sydney was supposed to be Valerie Bertinelli’s fabulous return to television after her successful run on One Day at a Time.

Sadly, there was nothing fabulous about this show. They canceled it after one season. Perry was quickly becoming the prince of the canceled show. If something didn’t stick soon, his career would be over.  

Screenshot: Matthew Perry looking at side surprised - from Numb (2007)Fries Film Group , Numb (2007)

11. He Was The King Of The Make Out Session 

Perry may have been the prince of the canceled show, but he was a king elsewhere. Perry seemed to have the royal habit of making out with beautiful women. 

Before she was a superstar, Perry made out with Gwyneth Paltrow in a closet. He also claims to have played tonsil hockey with Valerie Bertinelli—while her husband Eddie Van Halen was passed out in the next room. 

On a date with Cameron Diaz, however, he didn’t get a chance to kiss her—because she accidentally punched him in the face. 

He may have been lucky with women, but with TV shows? Not so much. 

Portrait of Gwyneth Paltrow smiling to the camera - 2011Baume & Mercier, CC BY-SA 2.0, Wikimedia Commons

12. Three Times Unlucky

After a stint on Beverly Hill 90210—where he played a tennis star with inner demons—Perry found himself on yet another sitcom. This was 1993’s Home Free, and this time, Perry was the lead. 

If the title doesn’t sound familiar, it’s because…you guessed it…it didn’t last more than one season. Perry must have been on the verge of calling it quits. Maybe he was just destined to be a guest or recurring character—because nothing else seemed to be working. 

But he had no clue what was coming his way. 

Screenshot: Matthew Perry wearing white shirt and tie ,looking up - from Home Free (1993)Universal Television ,Home Free (1993)

13. It Was About The Future

Maybe Perry was thinking about quitting show business, but he had one last chance. The show was LAX 2194and it sounded like a disaster. 

The synopsis is more than a little vague. It’s about people working as baggage handlers at the LA airport in…you guessed it…2194. Perry made the pilot, and all he had to do was wait for the inevitable rejection. 

Matthew Perry wearing black shirt and jacket is looking messy  - 2010s_bukley , Shutterstock

14. He Got A Call

While Perry was waiting for the call about the likely failure of LAX 2194, he was helping a friend get ready for an audition. This audition was for another sitcom that was getting good word of mouth. 

The title was Six of One and Perry’s friend was desperate to get a part on the show. Perry was selflessly giving his time to help his friend and then he got a phone call: Six of One wanted to see him for one of the roles. 

Screenshot: Matthew Perry looking shocked - from Numb (2007)Fries Film Group , Numb (2007)

15. He Had To Nail It

David Crane and Marta Kauffman were trying to cast their sitcom called Six of One. They were having trouble casting one of the characters—known for being sarcastic and funny—and for some reason no one had made the dialogue sparkle. 

Perry knew the script off by heart from all the rehearsing he’d done with his buddy. All Perry had to do now was nail the audition. Besides, the pressure was off. He still had LAX 2194 to fall back on. 

Screenshot: Matthew Perry is screaming in camera - from The Whole Ten Yards (2004)Franchise Pictures, The Whole Ten Yards (2004)

16. They Wanted Him

Once Perry had auditioned, Crane and Kauffman knew that they had the person they wanted for Six of One. What they didn’t know was that Perry still had his pilot in limbo. This meant that he couldn’t commit to Six of One

Once Crane and Kauffman had heard Perry, they couldn’t imagine anyone else doing the part. They were in a real pickle—and the solution came in an unlikely way. 

As it turned out, someone at Warner Bros had actually been at the taping of the LAX 2194 pilot. His note was this: you can hire Perry for Six of One, this show is never going anywhere. 

Matthew Perry with beard wearing white shirt and grey suit looking and smiling at camera - 1997Featureflash Photo Agency , Shutterstock

17. He Had No Idea

Perry got the role and the show got a name change: Six of One was now simply called Friends. In fact, they hired Perry on Friday and he had to start work the very next Monday. I’m sure Perry was wondering: Would this be another one season wonder? 

Now it seems ridiculous to even ask the question, but let’s not forget: at this time Perry had no idea that Friends would turn into an international phenomenon. Perry’s life was about to change big time. But could he handle it? 

Screenshot: Matthew Perry looking upset and talking with other man - from Friends (1994-2004)Warner Bros. Television, Friends (1994-2004)

18. He Knew What He Wanted

Before Friends, Perry had always been quite truthful about what he wanted in life. He wanted to be famous. He also wanted the money, the good seats at restaurants and he wanted all the attention. 

A certain expression comes to mind when thinking about Perry: “Be careful what you wish for”. Perry was getting what he hoped for, and it had the potential to destroy his life. 

Screenshot: Matthew Perry talking on the phone - from Friends (1994-2004)Warner Bros. Television, Friends (1994-2004)

19. We Copied Him 

One thing that made Perry stand out from the rest of the Friends cast was his way of speaking. Chandler had a way of putting the emphasis on what most would consider to be the wrong word in a sentence. Like: “Could I BE any hungrier”? 

It turned out that Perry developed this amusing habit as a child. Well, the habit caught on, and it would be no exaggeration to say that Perry has changed the way Americans speak—maybe permanently. 

Perry had the fame he wanted: Now what about the women? 

Screenshot: Matthew Perry is looking happy - from Friends (1994-2004)Warner Bros. Television, Friends (1994-2004)

20. She Wanted Him Only

One of the perks of being in a hit show is dating other celebrities. Friends was a huge hit and some major stars wanted to be guests on the show to increase their fame. One such star was Julia Roberts

Roberts messaged the show about appearing, but she had one big condition: She only wanted to be in Perry’s story line. An absolutely stunned Perry responded to this with three dozen roses. And what was Roberts’ quirky reply? She sent him a huge number of bagels. 

The flirtations had begun. 

Portrait of Julia Roberts smiling - 2018GabboT, CC BY-SA 2.0, Wikimedia Commons

21. She Was A Step Above 

You have to remember that Roberts was at this time a major motion picture star, while Perry was just famous for a sitcom. The two were not really on equal ground, but that didn’t seem to matter to Roberts. 

One thing that did keep them apart, however, was long distances. The two were in different parts of the country and there was no WhatsApp, no iMessage, and not even email existed yet. The two stars turned to the technology that was available at the time: fax.   

Portrait of Julia Roberts wearing sunglasses - 2016Georges Biard, CC BY-SA 3.0 Wikimedia Commons

22. He Was On Cloud Nine

After some flirty faxing, Perry and Roberts finally met up face to face and their relationship took off. This was even before Roberts filmed her Friends episode so any passion you see between them on her episode is pretty much real. 

Perry even went to New Mexico to bring in the new year with Roberts’ family. It was getting serious, and Perry couldn’t have been happier. He was, after all, dating America’s sweetheart. So what went wrong? 

Screenshot: Matthew Perry with rinsed hands - from The Whole Ten Yards (2004)Franchise Pictures, The Whole Ten Yards (2004)

23. He Nipped It In The Bud

Perry couldn’t believe that a movie star like Roberts wanted to date a lowly TV star like him, even though he was on the highest rated show on television. 

The thought that she would eventually realize that he was not worthy of her became an obsession for Perry. He was sure she would break it off, so he did the one thing that would stop this from happening: He broke it off first. Perry says he still remembers her confused face. 

He’d lost America’s sweetheart, so what about America’s hottest lifeguard? 

Screenshot: Matthew Perry is looking sad  - from Numb (2007)Fries Film Group , Numb (2007)

24. He Dated His Obsession 

Another star who was on Friends was Baywatch actor Yasmine Bleeth—well, sort of . Now Bleeth never actually appeared on Friends, but viewers heard her name an awful lot. You see, Perry’s Chandler—a diehard Baywatch fan—had an obsession over Bleeth and talked about her a lot. 

In 1996, a dream came true for Perry. The two got together and had a relationship that they kept hush hush from fans. Sadly, the relationship didn’t last. 

Perry may have been dating beauties, but he still had time for some good old fashioned payback. 

Yasmine Bleeth smiling and looking at camera - 1997Featureflash Photo Agency ,Shutterstock

25. He Proved Him Wrong

Back in high school, Perry had been a bit of a class clown and one of his teachers, Dr. Webb, had suggested that he didn’t have much of a future ahead of him if he didn't stop telling so many jokes. 

With the success of Friends, Perry had already proved this teacher wrong, but Perry wanted to rub the fact into the teacher’s face. When Perry made the cover of People magazine, he sent a copy of the issue to Dr. Webb. 

Clearly, Perry was now a big star. Big enough to turn down an award. 

Screenshot: Close up photo of Matthew Perry looking at side serious - from  Numb (2007)Fries Film Group , Numb (2007)

26. He Gave Them A Big No

The acting ensemble of Friends were a tightly knit group, and the six actors always had each other’s backs. When Perry received an Emmy nomination for best actor, he had a problem with it. 

How could there be a best actor in an ensemble comedy? Perry contacted the people at the Emmy awards and had his name removed from the nominations. The group had collectively decided they would only accept “supporting actor” nominations. 

The acting awards, however, weren’t always kind to the gang on Friends. Not at all. 

Screenshot: Matthew Perry is standing beside Lisa Kudrow and looking at laptop  - from Friends (1994-2004)Warner Bros. Television, Friends (1994-2004)

27. He Escaped 

Believe it or not, there are some people out there who don’t like the iconic sitcom Friends. The folks at the Razzie Awards—those infamous awards that celebrate the worst of things—could be some of them. 

In fact, they have handed out a nomination for worst actor to five of the six members of Friends. Lucky for Perry, he’s the only core cast member to escape the reviled Razzie awards. 

Perry may have missed out on a Razzie, but his luck was about to run out. 

Screenshot: Matthew Perry is looking at side surprised in dark - from Birds Of America (2008)Plum Pictures , Birds Of America (2008

28. He Had An Accident

When Friends was at its frenzied peak of popularity, Perry had a Jet-skiing accident. Along with the accident came some ongoing pain. Perry’s doctor innocently prescribed him with Vicodin for the pain. The doctor had no idea he was creating a monster. 

You see, with this one prescription, Perry found something out: The pills made him feel better than he’d “ever felt in his life”. 

Matthew Perry wearing white shirt, green jacket and blue sunglasses is looking at side happy on red background. - 2004DFree , Shutterstock

29. He Went Voluntarily 

It didn’t take long for Perry to become addicted to what the doctor had prescribed him. To combat this, Perry voluntarily went into rehab for addiction to Vicodin. 

In this case, the word “addiction” may be an understatement: He was taking 55 pills a day. His 28 day stay at the rehab center may have helped him with Vicodin, but Perry now had a few more issues to deal with. 

You see, he was still looking for that “feel good” feeling. If he couldn’t have Vicodin, he’d find something else. 

Screenshot: Matthew Perry is looking surprised at side - from The Whole Nine Yards (2000)Franchise Pictures, The Whole Nine Yards (2000)

30. His Issues Piled Up

Once Perry had beaten Vicodin, he now had another hurdle to overcome: His addiction to opiates. He took this in the form of the infamous medicine OxyContin, which led Perry back to rehab to try and get over that. 

Oh and don’t forget, in addition to Oxycontin, Perry had his drinking to sort out. At one point, he was downing a quart of the hard stuff every day. 

Somehow through all this, Perry was still working. The fans were still happy with their beloved Chandler. The suits at Warner Bros, however, had a big problem. 

Matthew Perry wearing black suit and grey tie is touching his chin and looking upset  - 2008Joe Seer , Shutterstock

31. He Put It On

The big wigs at Warner Bros had a concern about Perry—but they didn’t care about his drug issues, they cared about his appearance. 

You see, when Perry was using opiates he got really thin, and when he was drinking he tended to put on weight. It was the latter problem that made the bosses come down on Perry. They wanted him to lose weight. 

That’s when Friends buddy Jennifer Aniston offered to help by becoming his personal trainer, which kind of sounds like an episode of friends rather than real life.

Perry was going down a rabbit hole of addiction, and he was about to work with someone even worse off than he was. 

Portrait of Jennifer Aniston looking at side - 2012DFree , Shutterstock

32. He Put His Fist Through It 

In 1998, Perry appeared opposite funny man Chris Farley in Almost Heroes. Perry and Farley both had great comedic chops, but had something much darker in common: addiction issues. 

Farley made it through the filming, but passed five months later—and before the film premiered. It was then that Perry got more upsetting news: He had to promote the film without his buddy Farley. When Perry heard this news he was so angry, he put his fist through Jennifer Aniston’s dressing room wall. 

Perry’s life was spiraling out of control—but the at least movie deals kept coming. 

Screenshot: Matthew Perry in old military uniform, looking at side - from Almost Heroes (1998)Turner Pictures, Almost Heroes (1998)

33. They Made A Bet 

In 2000, Perry got a chance to be in the comedy The Whole Nine Yards with Die Hard’s Bruce Willis. During filming, Perry and Willis became friends, but they didn’t agree on something. 

Perry thought the movie would be a hit, but Willis didn’t. The two actors then made a bet: If the film was a success, Willis would have to appear on Friends and not receive any money for it. While this is a great story, some people think that it may not actually be true. 

Of course, Willis did appear on Friends, but he got his hefty paycheck. Nice guy Willis donated the entire amount to various AIDS charities and to underprivileged children. Apparently, there are nice guys in Hollywood—some you can even call friends. 

Screenshot: Bruss Willis is holding Matthew Perry by the neck - from The Whole Ten Yards (2004)Franchise Pictures, The Whole Ten Yards (2004)

34. He Wanted Out

Back on the set of Friends, the cast was starting to notice that Perry was having problems. One by one Perry’s Friends friends offered their support. Perry, however, couldn’t handle all the love and good will from some of TV’s most recognizable stars. 

He wanted to avoid the situation, and he reached out to his manager. All he wanted was a movie—any movie—that was out of town. 

Screenshot: Matthew Perry is looking upset and yelling  - from Friends (1994-2004)Warner Bros. Television, Friends (1994-2004)

35. He Had To Check In 

Perry’s movie to avoid dealing with his drug problem was 2002’s Serving Sara with Elizabeth Hurley. Everything was going well during the Texas shoot until Perry started having really bad stomach pain. This wasn’t just butterflies in his stomach because he was acting with the beautiful Hurley, this was real pain. 

Perry abruptly left the set, got on a plane, and checked himself into a hospital in Marina del Rey, California. There’s something fishy about this. Aren’t there any hospitals in Texas? 

Screenshot: Matthew Perry is looking at side - from The Whole Nine Yards (2000)Franchise Pictures, The Whole Nine Yards (2000)

36. The Truth Came Out 

So, why did Perry have to leave Texas for his stomach pains? The real reason is that he was checking himself into rehab. A few days later, Perry's publicist announced that Perry was indeed in rehab. The filming of Serving Sara had to continue, so the director just stuck to the scenes that didn’t include Perry. 

Somehow, Perry finished filming Serving Sara, but he was now about to face another ending: The ending of Friends

Elizabeth Hurley and Matthew Perry are talking - from Serving Sara (2002)Mandalay Pictures, Serving Sara (2002)

37. He Got The Last Word

The final episode of Friends, in 2006, had an audience of 52.5 million people. Perry had the distinction of saying the final line of the series. In the episode, the gang all decide to go for coffee and Chandler simply asks, “Where?”

If you don’t know why this is funny, It’s time to binge watch the 10 seasons of Friends. For fans, it was the end of an era. For the stars of the show, it was the end of a paycheck.

Perry was free to do what he wanted, but was having free time a good thing for the addiction-prone Perry? 

Screenshot: Matthew Perry is looking at side on the street - from Numb (2007)Fries Film Group , Numb (2007)

38. It Wasn’t Enough 

Perry didn’t want the freedom, so he got back on television. This was Studio 60 on the Sunset Strip, and Perry knew he wouldn’t be making the same big bucks he’d made back on Friends. Warner Bros offered Perry a measly $50,000 per episode to appear in the show. 

At its peak, Friends had paid Perry over a million dollars per episode. Could Perry’s self esteem suffer this financial setback? 

Screenshot: Matthew Perry looking at front with upset face - from Numb (2007).Fries Film Group , Numb (2007)

39. It Was Humiliating 

Warner Bros knew they had to sweeten the deal to keep Perry on board for Studio 60 on the Sunset Strip, so they offered him $175,000 per episode. While it was clearly still much less than on Friends, Perry knew this wasn’t going to be the cash cow that his previous show had been. 

He accepted the offer—but then he got some humiliating news: Matt LeBlanc was taking in $600,000 for his Friends spin off Joey. 

That had to hurt, but not as bad as losing a secret girlfriend. 

Matt LeBlanc wearing white shirt is looking at side and smiling to camera - 2012Kathy Hutchins , Shutterstock

40. He Kept Her A Secret

Throughout his career, Perry’s romantic life somehow managed to fly under the radar—at least compared to someone like Jennifer Aniston’s. In his memoir, Friends, Lovers and the Big Terrible Thing, Perry talks about a relationship that really shook him. 

For some reason, however, Perry failed to mention the woman’s name. Well, speculators have done their research and decided it was fellow Canadian—and Scream star—Neve Campbell

Back in 1999, the two were in Toronto making Three To Tango when sparks flew. The sad truth was that Campbell thought Perry’s addiction was a problem and walked away. 

Perry’s break up with Campbell was apparently quite amicable, unlike this more recent parting of ways. 

Actress Neve Campbell is looking and smiling at camera - 2009Phil Chapell, CC BY-SA 2.0 , Wikimedia Commons

41. She Couldn’t Hear His Name

In 2013, Perry had been dating Mean Girls star Lizzy Caplan for about seven years—or had he? During an interview, Caplan did something very odd: She covered her ears when anyone mentioned the name Matthew Perry. 

The secret eventually came out: They had broken up a year before the interview. Caplan did eventually explain the ear covering incident, saying, “I’m close with people who are far more famous, and they know how to avoid attention”.  

Huh? I think covering your ears during an interview is about as attention seeking as it gets. Maybe Perry was lucky to get out of that one. Luck, however, was once again not on his side. 

Portrait of Lizzy Caplan looking at side -  2014iDominick, CC BY-SA 2.0 , Wikimedia Commons

42. He Was Lucky To Be Alive

In 2018, Perry had an incident you don’t hear about everyday: His colon exploded. This led to Perry being in a coma for a whopping two weeks. 

While he was in the coma, doctors had to put Perry on an ECMO machine, a machine that performs the functions of your heart and lungs. At the hospital there were a total of five patients on an ECMO machine—only Perry survived.  

Maybe this near death experience had the potential to finally straighten out Perry’s life.  

Screenshot: Matthew Perry wearing black shirt and looking angry - from Numb (2007)Fries Film Group , Numb (2007)

43. He Faked It

Over the last few years, Perry has still struggled with addiction. As recently as 2020, Perry was in rehab in Switzerland. While there he pretended to have pain so he could get a prescription for Oxycontin—and he talked them into giving him 1,800 mg per day. 

Later, when he needed surgery, they made the mistake of giving him the anesthetic propofol. That was when his heart stopped. 

Screenshot: Matthew Perry is talking with woman and looking sad - from Birds Of America (2008)Plum Pictures , Birds Of America (2008)

44. He Said Goodbye

After Perry’s heart stopped, the people at the hospital in Switzerland sprang into action. They performed emergency CPR, breaking eight of his ribs in the process. 

Perry woke up—11 hours later—and didn’t recognize his hospital room. That’s because they’d moved him to a different hospital. From then on, the doctors refused to give him any medication. That’s when Perry decided it was time to say Auf Wiedersehen to Switzerland. 

Matthew Perry wearing black suit and tie is smiling and looking up, waving with hand - 2012Kathy Hutchins , Shutterstock

45. He Made A Quick Crossing

Before he booked his flight back to LA, Perry made sure the hospital there would give him what he wanted: 1,800 mg of Oxycontin a day. Once he’d confirmed that, Perry didn’t waste any time getting back to the states. He hired a private jet for $175,000 to get him there in privacy. 

When he arrived at the hospital in LA, he was in for a rude awakening: They actually wouldn’t give him the amount of Oxycontin he thought he needed. 

All the money in the world couldn't convince the doctors to give him what he wanted. What could this poor rich guy do? 

Screenshot: Matthew Perry is yelling and pointing to the water  - from The Whole Nine Yards (2000)Franchise Pictures, The Whole Nine Yards (2000)

46. He Took A Round Trip

Perry had just spent $175,000 flying from Switzerland to LA only to find that the doctors there wouldn’t prescribe him such a huge amount of Oxycontin. The doctors explained that even cancer patients only get 100 mgs per day. How could they possibly prescribe 1,800 for him? 

Perry didn’t care for their reason, he knew what he wanted, and he knew where he could get it. He jumped back on the plane—and spent another $175,000—to go back to Switzerland. I guess flying coach was out of the question. 

$350,000 on a couple of flights was just a drop in Perry’s enormous bucket of cash. But even for a rich guy like Perry, his addictions had cost him a lot. 

Screenshot: Matthew Perry is looking up scared - from The Whole Ten Yards (2004)Franchise Pictures, The Whole Ten Yards (2004)

47. He Was Sweating And Twitching 

In the end, Perry claims that he has spent approximately $9 million trying to beat his addictions. He also says he has been in rehab on 65 separate occasions. In addition to this, his AA meeting total is 6,000. 

One of his low points came when he was in rehab and watching the Academy Awards with a few of his fellow addicts. This was the year that Julia Roberts won Best Actress for her role in Erin Brockovich. His ex-girlfriend was winning an Oscar and he was in rehab doing what addicts do: “sweating and twitching”. 

Surely there were good times ahead for Matthew Perry, weren't there?

Matthew Perry is talking and touching his face - 2003Featureflash Photo Agency , Shutterstock

48. He Took A Bite

By the time there were plans for a Friends reunion, Perry seemed to have all his ducks in a row. He wasn’t using medication, booze, and he even had quit his 60-smokes-a-day addiction. 

Days before the filming of the reunion began, Perry took a bite of a toasted peanut butter sandwich. While most of us do this without incident on a daily basis, when Perry did it it became a nightmare: All of his teeth fell out. 

Perry had no teeth and had to film one of the most anticipated reunions in TV history in a few days. 

Cast of sitcom Friends seating on sofa, talking and smiling - from  Friends: The Reunion (2021)Warner Bros. Unscripted Television, Friends: The Reunion (2021)

49. He Mumbled

Perry’s dentist had to remove all of the actor’s teeth and even the implants attached to his jaw. Once the good dentist had removed pretty much everything in Perry’s mouth, Perry got a whole new set of teeth. 

This was all done at lightning speed before the taping of the reunion. Perry got to the taping looking great—he just didn’t sound too great. The dental work caused his speech to sound like he was mumbling, which made some viewers think he’d downed a few shots before the show. 

Perry later confirmed that he had not had an addiction relapse. Perry has been managing to hold his addictions together. Maybe now he can find someone to love. 

Jennifer Aniston and Matthew Perry seating and talking - from  Friends: The Reunion (2021)Warner Bros. Unscripted Television, Friends- The Reunion (2021)

50. They Didn’t Make It 

Perry survived the Friends Reunion, and set course on a new romantic adventure. Perry’s most recent relationship went further than all the previous ones: He actually proposed. In November of 2020, Perry asked literary manager, Molly Hurwitz, to be his wife. 

They’d started dating in 2018 and announced it two years later on Instagram. Sadly, they didn’t make it to the wedding day. The relationship was kaput by June 2021.

Matthew Perry looking sad at camera - 2009Featureflash Photo Agency , Shutterstock

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Dark Family Secrets Exposed

Nothing stays hidden forever—and these dark family secrets are proof that when the truth comes out, it can range from devastating to utterly chilling.
April 8, 2020 Samantha Henman

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Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.

Madame de Pompadour Facts

Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
December 7, 2018 Kyle Climans

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I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.

These People Got Genius Revenges

When someone really pushes our buttons, we'd like to think that we'd hold our head high and turn the other cheek, but revenge is so, so sweet.
April 22, 2020 Scott Mazza

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Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.

Catherine of Aragon Facts

Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but very few people know her even darker history.
June 7, 2018 Christine Tran

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