Don Rickles was a shameless comedian who had a humiliating snub for anyone who wandered into his path. He did have one secret, however, and it had the potential to undermine his entire career.
1. He Wanted Two Things
No one could volley a dig quite like Don Rickles. He was the master of insults and carelessly disparaged singing stars, mobsters, and even a First Lady. Besides all the snubs, there were two other things that Rickles wanted to achieve in life.
He wanted respect as a dramatic actor and his own successful TV show. With a career spanning more than six decades, he may just be able to pull them both off. Read on and see.
2. He Signed Up For Drama
Don Rickles, born in Queens, New York on May 8, 1926, went straight from being the class clown in high school to something a lot more serious. During WWII, Rickles volunteered for a very dangerous job launching torpedoes. Luckily, Rickles survived the experience and was soon ready to go home and start his boring life.
Well, that didn’t quite happen.
Metropolitan Transportation Authority, Flickr
3. He Couldn’t Follow
Rickles’ plan after WWII was to follow in his father’s footsteps, which—sadly enough—was a mundane job in insurance sales. Not only was it dull, Rickles wasn’t any good at it. Rickles desperately needed to find something else and out of the blue decided on acting. His first move was to enroll at the American Academy of Dramatic Arts.
Once he graduated, he found out the depressing truth.
Epicgenius, CC BY-SA 4.0, Wikimedia Commons
4. He Turned It Around
After finishing at the American Academy of Dramatic Arts, Rickles realized that no one really wanted to hire him as an actor. That’s when Rickles remembered he’d been the class clown in high school and decided to turn his career around. If people didn’t want to see him be dramatic, he’d be the funny guy.
Well, for some reason, this funny guy brought out the worst in people.
Joseph Scandore-management, Wikimedia Commons
5. He Was Mean
Rickles’ stand up act seemed to attract a lot of audience participation. Mostly this was in the form of annoying hecklers calling out insults from their seats. It was what Rickles did with the hecklers that really made him stand out. He quickly became known as a comedian who served the best, and most hilarious, insults back to his hecklers.
There was one problem though. Now, the hecklers wouldn’t leave him alone.
6. He Picked On Them
Rickles took the art of insulting audience members to a whole new level. Before long, Rickles' cruel interactions with audience members—who he called “hockey pucks”—had become the main source of his comedy. In fact, his act was now almost completely ad libbed insults. People started calling him the master insult comic.
Rickles soon went from picking on hecklers to picking on pretty much anyone in the audience. Even people who could get him into deep trouble.
7. He Insulted A Very Important Lady
At one performance, Rickles saw that President Franklin Roosevelt’s son was in the audience. He addressed the President’s son directly. He told him he’d seen the first lady in Vegas. This was, of course, Frank Junior’s mother. Rickles risked offending the US president by saying that Eleanor Roosevelt was in Vegas looking to have a good time with sailors.
It was a very brave and hilarious move. His next one, however, had the potential to cause him severe bodily harm.
National Archives and Records Administration, Wikimedia Commons
8. He Risked His Wrath
Rickles was doing a show in Miami Beach, Florida when he noticed Frank Sinatra in the audience. Not only was Sinatra a huge singing and acting sensation, he also had a scary reputation because of his connection with mobsters. Rickles had to make a decision. Insulting Sinatra could get him into a lot of trouble, but doing it would be so much fun.
Capitol Records, Wikimedia Commons
9. He Knocked Him Off His Seat
Rickles couldn’t help himself, so he threw an insult in Sinatra’s direction. Knowing about the singing star’s temper, he told him to make himself at home and “hit somebody”. Rickles had to wait in fear as Sinatra realized that he was the punchline of this funny man’s jokes. As the story goes, Sinatra laughed so hard he fell off his chair. Rickles knew he’d made the right decision.
With Sinatra as a fan, the only way was up.
NBC Television, Wikimedia Commons
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10. He Got Big
Sinatra was one of the most well connected people in show business, and he was soon encouraging his celebrity friends to go to Rickles’ shows and get their own dose of insults. Sinatra even had a nickname for Rickles, “Bullet-head”. With Sinatra’s connections, Rickles went from performing in small venues to headlining in Las Vegas.
The bigger Rickles got, the nastier his comments became.
11. They Asked For It
Rickles got so famous for his insults, that people were actually lining up to get one. Iconic comedian Carl Reiner said that a lot of people in show business felt that getting an insult from Rickles would put them on the map. On the other hand, if you didn’t receive an insult, it meant that you “weren’t with it".
“Insultmania” was taking over America, and Rickles had no choice but to take it to a higher and scarier level.
Rogers & Cowan, Wikimedia Commons
12. They Feared Him
Rickles' insults became so infamous that he got another nickname, “The Merchant of Venom”. To make him sound even scarier, when he appeared on a talk show, the band would usually play a matador melody. Like a bull, he was about to gore the audience. Rickles was on top of the world of insult comedy, but he hadn’t forgotten his dream to be a dramatic actor.
Because of his reputation as a funny man, Rickles realized that no director would want him for a dramatic role. He had to get aggressive.
13. He Was Perfect
Rickles heard about a film that he thought he’d be perfect for. It was about a WWII submarine crew and, because of his involvement on the torpedo boat, it would be right up Rickles alley. There was, however, a problem. The film already had a star-studded cast, and Rickles had absolutely no experience as a dramatic actor.
Rickles’ plan was to somehow get a part in this movie and turn his career around completely.
Hecht-Hill-Lancaster Productions, Run Silent Run Deep (1958)
14. It Was The Joker Versus The Riddler
Run Silent, Run Deep already had superstars Clark Gable and Burt Lancaster attached to it. There was one role still up for grabs that Rickles desperately wanted. The bad news was that Frank Gorshin—who played The Riddler opposite Adam West’s Batman—also wanted the role. Most people thought that Gorshin was a shoe in for the part.
Rickles refused to give up and doggedly pursued the role. As it turned out, luck was on his side.
Hecht-Hill-Lancaster Productions, Run Silent Run Deep (1958)
15. He Took It Away
Gorshin definitely wanted the part in Run Silent, Run Deep, and got in his car and started a grueling 39-hour drive to Hollywood for his audition. Somewhere on the way, he crashed his car and ended up in a coma. When Rickles learned of Gorshin’s condition, he swooped in and took the role from the hospitalized actor.
Now, he just had to prove he could act.
Hecht-Hill-Lancaster Productions, Run Silent Run Deep (1958)
16. He Didn’t Have A Clue
Rickles was in a major film with some of Hollywood’s biggest stars. The thing was, he didn’t really know what he was doing. One thing that puzzled him was how the other actors memorized their lines so quickly. When he discovered he couldn’t do it, he had to get sneaky.
Rickles wrote his lines out on paper and secretly hid them on set. Problem solved. Rickles could certainly learn a lot from his co-stars on this film. Sadly, he had no intention of doing that.
Hecht-Hill-Lancaster Productions, Run Silent Run Deep (1958)
17. He Lied
The actors playing in Run Silent, Run Deep had to pretend to be able to operate some pretty technical submarine equipment. Rickles’ co-star Burt Lancaster made his acting more believable by learning what all the machinery actually did.
Rickles simply smiled and told Lancaster that he had done the same. Something that was completely untrue. Rickles did survive this dramatic movie beneath the sea, and followed it with a ridiculous one on the shore.
Hecht-Hill-Lancaster Productions, Run Silent Run Deep (1958)
18. He Hit The Beach
It turned out that Rickles’ agent was the husband to teen star Annette Funicello, and somehow they talked Rickles into appearing in one of her Beach Party films. This was Beach Blanket Bingo and in it Rickles does his stand up routine. Another actor in the film, silent film star Buster Keaton, completely embarrassed Rickles.
A camera caught Keaton looking completely bored during Rickles’ set. Rickles got a lot of teasing for doing a juvenile Beach Party film—even at the White House.
Alta Vista Productions, Beach Blanket Bingo (1965)
19. He Needed To Relax
Years later Rickles was at the White House with then President George HW Bush and his wife Barbara. Likely Rickles was on his best—and maybe a little boring—behavior. For some reason the First Lady suddenly surprised Rickles by teasing him for being in Beach Blanket Bingo. It was likely the ice breaker that Rickles needed to relax with the President and his wife.
Beach Blanket Bingo was full of scantily clad beauties. Sadly, Rickles life had exactly zero of these. That, however, was about to change.
Alta Vista Productions, Beach Blanket Bingo (1965)
20. He Lived With His Mom
While Rickles was certainly on top of his game when it came to insult comedy, this certainly didn’t attract a whole lot of women. In fact, he was just short of 40 and still—embarrassingly so—living with his mother. It was clear that Rickles didn’t have a magic touch with women like his buddy Sinatra did. His style of flirting was…well…let’s call it interesting.
21. He Couldn’t Resist
One day, Rickles was on the phone with his agent’s office, and trying to get the secretary to give him an appointment. When Barbara Sklar asked Rickles why he wanted to see the agent, Rickles sarcastically told her that he was a butcher selling meat. Sklar didn’t laugh, and Rickles immediately became intrigued—intrigued enough to make her his wife on March 14, 1965.
Rickles had done the impossible and won over Sklar. Next on his list was winning over Johnny Carson.
22. He Did It A Lot
The iconic talk show—The Tonight Show Starring Johnny Carson—was in its third season, and Rickles was desperate to get on it. Rickles did get the invite and was nervously waiting to see how it would go. Well, the pairing of Rickles and Carson was pure gold. In fact, Rickles returned to Carson’s show more than 100 times.
NBC, The Tonight Show Starring Johnny Carson (1962–1992)
23. She Had No Idea
When Rickles was performing in Vegas, his wife was often stuck hanging around waiting for him to finish. One night she met another wife of comedian Bob Newhart’s and the two women became fast friends. Newhart’s wife, Ginnie wanted the two couples to meet for coffee as Ginnie had no idea who Rickles was.
Well, Ginnie was in for the surprise of her life.
Alan Light, CC BY 2.0,Wikimedia Commons
24. He Shocked Her
The Rickles and the Newharts did go for coffee, and Ginnie Newhart thought Rickles was “such a sweet man”. Later, when in front of an audience, Rickles showed Ginnie his true colors. He introduced the Newharts in his usual fashion, even going so far as to call Bob Newhart a "stammering idiot from Chicago". He’d shocked Ginnie’s socks off, but still the two couples formed a tight friendship.
Rickles and Newhart were absolute opposites on stage, but something absolutely adorable bound them together.
25. They Formed A Club
The Las Vegas scene was full of cheaters and womanizers. What solidified the Rickles and Newhart friendship was that neither of them wanted to cheat on their wives. The two adorably became a two person no-cheaters club, and the friendship soared from there. It wasn’t, however, always best friends forever for these two jokers.
Ron Galella, Ltd., Getty Images
26. It Was A Love Hate Kind Of Thing
Yes, Rickles and Newhart were close friends, but they also took shots at each other. Rickles said of Newhart, "Bob's a brainy kind of comedian and I'm a kind of guy that gets laughs". Nice guy Newhart didn’t hold back in getting his revenge. He said that Rickles was his “best friend, which just gives you some idea of the difficulty I have in making friends”.
Rickles now had a best friend. Good, cause he’d need emotional support for his next two failures.
27. He Had Two Strikes
Rickles had done so well on Johnny Carson’s show, he thought he’d try it himself. In 1968 he came out with The Don Rickles Show. As it turned out Rickles was a better guest than he was a host. The variety show tanked after just 17 episodes. Sadly, Rickles didn’t learn his lesson. He used the same title for a sitcom in 1972, which lasted just one season.
Rickles next humiliation would be to come crawling back to Carson’s show as a guest.
Unknown Author, Wikimedia Commons
28. He Was Clumsy
Rickles was soon back on The Tonight Show Starring Johnny Carson only to find Carson not there. Instead there was Rickles best bro Bob Newhart. Surely Carson wasn’t avoiding him, or was he? This question may have made Rickles a little nervous that night, as he clumsily broke a wooden box on Carson’s desk.
When Carson saw the broken box, he set out to make Rickles pay. 
NBC, The Tonight Show Starring Johnny Carson (1962–1992)
29. He Got Pranked
At the time, Rickles was working on yet another TV show—CPO Sharkey—which just so happened to film next to Carson’s studio. During his show, Carson grabbed a cameraman and the broken wooden box and crashed Rickles' set looking furious. Rickles was clearly not expecting a visit from Carson, and this “on the move” prank went down in TV history.
NBC, The Tonight Show Starring Johnny Carson (1962–1992)
30. He Met A Hero
When Superman's friend Jimmy Olsen went rogue, he had an encounter with Rickles. You see, DC artist Jack Kirby introduced a series of comics with Olsen as the main character. In a bizarre story line, Olsen’s character actually meets Rickles. The insult comedian’s name even made it into the title of the comic: “Will the Real Don Rickles Panic?”
Meeting Jimmy Olson only increased Rickles’ fame. Soon he wasn’t safe to walk the streets at all.
Susan Skaar, CC BY-SA 3.0, Wikimedia Commons
31. He Gave Random Insults
At this point in Rickles’ career, fans often recognized him on the street, and he always tried to be nice. Nice, however, is not what his fans wanted from him. Fans wanted to get an insult from him. Bizarrely, many men wanted him to disparage their wives. Rickles had trouble saying no to his adoring fans and usually obliged them with an insult.
Another person Rickles couldn’t say not to was Frank Sinatra.
Bert Verhoeff, CC0, Wikimedia Commons
32. He Switched Teams
When Republican Ronald Regan became the US president in 1981, he turned to Frank Sinatra to croon him into the White House. Sinatra gave Rickles a tap on the shoulder to join him, and Rickles, as a staunch Democrat, was desperate to say no. Well, Sinatra twisted Rickles arm until he got the answer he wanted. Rickles had to become a Republican for one night.
Rickles needed to learn to say no. It may have saved him from appearing in this turkey of a movie.
Michael Evans, Wikimedia Commons
33. He Was In A Stinker
Back in 1970, Rickles made an adventure comedy called Kelly’s Heroes, and on the set he met a nerdy 18-year-old errand boy. Surprisingly, this kid grew into hotshot The Blues Brothers director John Landis. Well, Landis remembered Rickles and wanted him for his 1992 much anticipated vampire film Innocent Blood.
Rickles said yes and walked innocently into this stinker of a film that one pain in the neck critic even called “anemic”. Rickles needed a hit project, and he turned to his arch enemy: TV.
Giorgio Montersino, CC BY-SA 2.0 , Wikimedia Commons
34. He Tried It Again
Rickles came off of his disastrous turn in a vampire movie only to try another sitcom. In September, 1993, Rickles appeared in a show about a well educated psychologist who lives with his much more down to earth—and sarcastic—dad. Hmmm…if the son was played by Kelsey Grammer I’d say you had Frasier on your hands.
Nope this was Daddy Dearest, and it was up against some very tough competition.
35. He Went Head To Head
Not only was Rickles’ Daddy Dearest walking a similar path as Frasier, the two shows premiered in the same month. It was soon pretty clear which show won the hearts of audiences. Frasier would go on to an impressive 11 seasons and Daddy Dearest…well…it did last 11 episodes. A failed sitcom following a failed movie.
Things were not looking good for Rickles. One more strike and he’d be out.
36. He Got A Break
As it turned out, one of the leading directors in Hollywood had a soft spot for comedians, and he came knocking on Rickles’ door. This was Martin Scorsese and the film he was casting promised to be a big hit, Casino. It may have been Rickles’ jokes that drew Scorsese to the insult comedian, but then Scorsese threw Rickles a surprising curveball. 
D@LY3D, Flickr
37. He Took On De Niro
The part Scorsese offered Rickles was not exactly going to use Rickles' strong suit. The role had almost no dialogue. So, Scorsese had set Rickles on mute for this film, but that didn’t stop the funny man from wisecracking between takes. He especially enjoyed taking potshots at costar Robert De Niro and his oh-so-serious method acting.
Scorsese had taken away Rickles’ voice. His next role would completely remove his body.
38. He Was A Potato
Superstar Toy Story writer and director John Lasseter sat down with Rickles and made an announcement. He told Rickles that he was the voice of Mr Potato Head. Rickles wasn’t having any of it and barked back at Lasseter that he didn’t do cartoons.
Rickles eventually calmed down and went on to make a fortune playing Mr Potato Head in three films and a theme park attraction. Rickles was getting on in age and should have been making up his bucket list. Instead, he appeared on someone else’s.
39. He Was On A List
Rickles must have been more than surprised when Kathy Griffin called him up and said he was on her mother’s bucket list. The news flattered Rickles, and he agreed to give Griffin’s mom the surprise of her life on Kathy Griffin: My Life on the D-List. If Rickles felt special, he shouldn’t have. Other things on mom’s bucket list included going out for dinner and having a good night's sleep.
If Rickles did want to feel special, he only had to look to this next very popular talk show host.
gdcgraphics, CC BY-SA 2.0 , Wikimedia Commons
40. He Had A Major Complaint
Jimmy Kimmel was a huge Rickles fan and once hosted a dinner for his idol at an LA restaurant called Mozza. At the end of the very costly meal, Rickles told Kimmel, “I can’t believe you took me to a pizza place". Rickles’ remark didn’t offend Kimmel. The big question on many lips was how Rickles got away with the incendiary things he said.
41. He Got Away With It
One of Rickles’ potentially offensive jokes was when he spoke to a Black member of the audience and said, “You’re Black, I’m white. It’s the breaks”. The word on the street was that actor Sidney Poitier was not a fan of jokes like these. And yet when it came to speaking about Rickles publicly, Poitier talked about how “explosive," “impactful,” and “funny” Rickles was.
It seemed that no matter how hard he tried, Rickles couldn’t ruffle a single feather. As it turned out, there was a darn good reason for this.
42. He Didn’t Discriminate
Not much was off limits when it came to Rickles’ insults. He could make fun of ugly people, gay people, even ethnic humor was a “go”. One thing that most critics agree on was that at least Rickles didn’t discriminate. Everyone was a potential victim.
Rickles had spent his entire life being offensive and yet, at the age of 90, there was one thing he still hadn’t accomplished and he hoped it wasn’t too late.
43. They Lined Up
Rickles still hadn’t had his own successful TV show, and he had only one last chance. The new show idea was to simply film Rickles having dinner with different celebrities. When word got around about the concept, celebrities were lining up in droves to dine with Rickles.
Among the guests on Dinner With Don were Billy Crystal, Amy Poehler, Robert De Niro, and Sarah Silverman. The show was a hit. Sadly, Rickles would never see his Emmy nominated series hit screens.
Stamper Lumber Company , Dinner with Don (TV Series 2017)
44. He Made Him Cry
On April 6, 2017, Rickles passed at home of kidney failure at the ripe old age of 90. One of the first to acknowledge this sad event was funny man Jimmy Kimmel. At the top of ABC’s Jimmy Kimmel Live, Kimmel announced that this was not going to be a normal show.
He told the audience about the loss of Rickles and then admitted that he was going to cry, ”probably a lot”. Kimmel knew Rickles well and he knew his secret. There was much more to the man than just insults.
45. He Wasn’t What We Thought
Yes, Rickles was the master of the insult, but he may have wanted to keep his true character a secret. You see, people actually called him “kind and generous and warm” and “a pussycat in wolf’s clothing”. He also had a lifelong marriage, which he referred to in his Vanity Fair Proust Questionnaire. He said, “Perfect happiness is having a wife who loves you”. Awwww.
Of course he couldn’t resist a little zinger at the end, “...and doesn’t ask for too much jewelry”.
Gary Dunaier, CC BY 2.0, Wikimedia Commons
46. He Was Crazy
Remember back when Rickles insulted Frank Sinatra during a show, well he went a step further when he picked on a very dangerous mobster named Crazy Joe Gallo. Thankfully Gallo, like Sinatra, enjoyed the insults and even asked Rickles to join him for his birthday dinner. Rickles had to decide. Insult the Gallo by saying no, or go out on the town with a known felon.
US-amerikanischen Bundesregierung, Wikimedia Commons
47. It Was A Near Miss
In the end, Rickles declined the invitation from Gallo and, because of that, lived to see the light of day. When Gallo and his family and friends were dining at the infamous Umbertos Clam House that night, armed gunmen entered and opened fire. When the smoke cleared, Gallo’s lifeless body was lying on the floor. It was a shocking near miss for Rickles.
Rickles next brush with danger would, thankfully, be safely between the pages of a comic book.
Paul Sableman, CC BY 2.0, Wikimedia Commons
48. He Was Unexpected
On one episode of The Tonight Show Starring Johnny Carson, Carson was doing a sketch where he got a strange and hilarious massage from two women. The sketch had already gone on for quite a while, when Rickles wandered on to the set. Carson seemed quite authentically surprised to see Rickles there, and his random presence left the audience in stitches.
This sketch went way overtime, and Rickles was going to have to pay.
NBC, The Tonight Show Starring Johnny Carson (1962–1992)
49. He Made It Long
Chuck LaFille hosted a game show called Beat The Clock, but at the moment he was probably imagining beating Rickles. You see, Rickles had made Carson’s sketch go on way too long and had bumped LaFille’s appearance right off the show.
Rickles eventually sauntered off the stage and saw the furious LaFillle who was now shouting about never doing the Carson show again. It was the wrong time for one of Rickles’ famous insults. But Rickles couldn’t resist.
NBC, The Tonight Show Starring Johnny Carson (1962–1992)
50. He Made An Enemy
Rickles took one look at the fuming LaFille and said,"Not the first time you lost a gig Chuckie!" LaFille was not up for one of Rickles barbs and pounced on him. Thankfully Carson’s right hand man, Ed McMahon was nearby and pulled LaFille off of a very shaken Rickles. It seemed that Rickles' acerbic personality certainly had the potential to make enemies.
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