By all accounts, Golden Age legend Frank Sinatra was a man who was not to be messed with.
There are many who suggest the crooner-turned-film-star had mob ties, and those who crossed him feared
retribution.
While most were afraid of messing with Frank, there was one man who had the courage to push
his buttons.
That man was insulting comic Don Rickles.
The reason that Frank put up with Don’s abuse was that they were lifelong friends.
Still, there was one prank that almost went too far.
Join Facts Verse as we explore how Don Rickles pranked Frank Sinatra and he never saw it
coming.
Don Rickles Could Get Away with Saying Almost Anything
When Don Rickles passed away in 2017, he left behind a legacy to be reckoned with.
The insult comedian grew to prominence as a figure on late-night talk shows.
Whereas most performers spent their time trying to get the audience on their good side, Don
was a performer who wasn’t afraid to get on their bad side.
Don became so proficient at his insult comedy that audiences would fear him, but they still
couldn’t help but tune in to see what the comedian was going to say next.
Don Rickles’ fearless insult comedy led to him garnering the nickname of “Mr. Warmth”
during his career.
Of course, the nickname was meant to be ironic.
Don was as cold as could be, though that didn’t mean that the man didn’t have a soft side.
Don held many friendships over the course of his career and even tried his hand at romance
one or two times.
However, the insult comedian’s cold nature on the stage and his comparatively warmer
personal life oftentimes butted heads.
Sometimes, Don couldn’t help himself from using his insult comedy skills against the
people he loved, and this included Frank Sinatra.
Don and Frank were buddies from their Las Vegas days and remained friends throughout
their lives.
In the history of Hollywood, there are few figures that have commanded quite as much
respect as Frank Sinatra.
For the most part, Frank maintained this respect deservedly.
The singer-turned-film-star was a rightful icon of Hollywood’s Golden Age who started
out as a pop crooner before becoming a highly acclaimed actor on the screen.
The star was also a legend in the aforementioned world of Las Vegas, where he wasn’t afraid
to let his wild side show.
Las Vegas is where Frank started up his friendship with Don Rickles, and the two had crazy times
there the likes of which we’ll never know.
Frank Sinatra Was an Icon That Was Feared and Revered
While Frank Sinatra was rightfully respected in the entertainment industry for his talents,
he was also feared for his alleged mob ties.
This was another reason that the average person was afraid to cross the star.
However, Don Rickles wasn’t the average person.
Don was an insult comic first and foremost, and this often bled into his friendship with
Frank Sinatra.
Their close and personal relationship led to Don becoming one of the only figures that
could make fun of Frank Sinatra without fear of facing some kind of retribution.
For the most part, Don Rickles got away with keeping up his insult-comic appearances during
his interactions with Frank Sinatra.
Don Rickles wasn’t afraid to publicly greet Frank upon the singer’s arrival at parties
by telling him to make himself at home by hitting one of the guests.
Domestic violence certainly wasn’t a topic that most would bring up around Frank Sinatra
lightly, though Don was able to get away with saying such things as a result of his and
the singer’s close bond.
Though Don got away with poking fun at Frank Sinatra publicly on numerous occasions, there
was one prank he pulled on the crooner that seems to have crossed the line.
The incident occurred when Don Rickles was dating a woman who refused to believe that
the insulted comedian was a close and personal friend of Frank Sinatra’s.
According to the late Frank Sinatra himself, Don pulled him aside while the two were dining
at the same restaurant and asked him a personal favor.
Frank claimed that Don asked him to come up to his and his date’s table and begin making
conversation to show that the two were friends.
Frank agreed to perform the request, though things didn’t turn out the way that the
singer was expecting.
Frank Sinatra says that he went up to Don and his date’s table and began making conversation
only for the insulted comedian to act as if the crooner was imposing.
This certainly impressed the woman that Don was dating, but it didn’t impress Frank
Sinatra!
Don took things too far with this prank, and Frank got his revenge with a prank of his
own.
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Frank Sinatra Was Pissed About Don Rickles’ Prank
When Don Rickles humiliated Frank Sinatra with his restaurant prank, the crooner became
very upset.
He decided that he was going to get revenge on his longtime friend.
Frank knew he was going to have to do something huge if he was going to get even, so he started
planning the biggest prank he could.
At the time, Don Rickles was performing at the Sahara Las Vegas.
Frank decided that he was going to have Don Rickles arrested in the middle of one of his
performances.
When the event went down, Don had no idea why he was getting arrested, and neither did
the audience!
The two police officers that whisked away the insult comedian while he was on the stage
ended up bringing him to the table of Frank Sinatra, and it was then that Don realized
what had happened.
At first, Don feared that he was going to lose his gig at the Sahara Las Vegas.
Thankfully, this didn’t end up happening!
Still, Frank undeniably got even.
Though Frank Sinatra certainly wasn’t happy in the moment when Don Rickles performed his
memorable restaurant prank on him, the story ended up becoming one of the crooner’s favorites
to recount.
Frank memorably told the story on The Tonight Show Starring Johnny Carson, where it was
forever immortalized.
Despite the prank war that ensued between Don and Frank, the two remained friends up
until the latter figure’s death in 1998.
Upon Frank Sinatra’s passing, Don Rickles acted as one of the fallen star’s pallbearers.
Nearly two decades later, Don himself would pass away at the age of 90.
Though Don Rickles and Frank Sinatra could get on each other’s bad sides, they also
saw the good in one another until the very end.
In addition to being some of the only people that could make fun of the other without risking
retribution, they were also two of the only people that could truly see the humanity in
each other.
Frank Sinatra’s high standing often made it hard for him to connect with people, and
Don Rickles has similar problems as a result of his ice-cold comic persona.
The two formed an unlikely bond that stood the test of time, and it resulted in some
incredibly memorable stories!
Don Rickles Came Up in Show Business the Hard Way
Don Rickles was born in Queens, New York, in May of 1926.
The future insult comedian set his sights on stardom at a young age and worked incredibly
hard to get the relatively modest amount of fame that he did over the course of his lifetime.
During the days of World War II, Don served his country by working in the Philippines
as a seaman.
By the time he got back from serving in the war, Don had refined his comedic talents and
was ready to start performing on the stage.
Don achieved fame in the entertainment industry via decades of hard work, and he eventually
became a notable figure to the public thanks to his appearances on late-night talk shows.
The comedian was also a legend in the aforementioned world of Las Vegas, where he met Frank Sinatra.
Other famous figures that Don Rickles maintained close friendships with include Bob Newhart.
Though Don Rickles’ success was mostly relegated to the world of insult comedy over the course
of his career, he found unlikely fame on the big screen during the 1990s.
In 1995, he took on a dramatic role in Martin Scorsese’s epic crime drama Casino.
The performance not only paid tribute to the insult comedian’s Las Vegas roots, but it
also paid tribute to his ongoing mob-adjacent friendship with Frank Sinatra.
Though Don’s legacy remains as a comedian first and foremost, it also remains frightening
how well he stepped into the role of the intimidating crime boss that he played in Casino.
While Don Rickles’ role in Casino proved to audiences that the insult comedian was
just as tough as he was funny, he also took on another screen role during the 1990s that
made him popular with a whole new generation.
In 1995, Don Rickles voiced the character of Mr. Potato Head in the classic CGI-animated
film Toy Story, and he reprised the role several times before his death in 2017.
The Toy Story films have made Don Rickles’ voice familiar to generations of kids.
When they’re older, they’ll get the chance to appreciate for themselves the tale of how
Don Rickles pulled one over on Frank Sinatra and then received the crooner’s wrath in
a big way.
Though Don Rickles and Frank Sinatra sometimes took their pranks on one another too far,
they remained lifelong friends.
Now it’s time to hear from you: did you know that Frank Sinatra had Don Rickles arrested
as a result of a prank war while the latter figure was performing on stage at the Sahara
Las Vegas and that the two remained friends until Frank’s 1998 death?
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