Mike Tyson’s circle of celebrity friends, including Hollywood icons, a US President and tennis queen Serena Williams

MIKE TYSON was known for making plentifulness of enemies successful a brutal heavyweight vocation that saw him labelled The Baddest Man connected the Planet.

But that vocation besides saw him marque a multi-billion dollar ellipse of friends - from chap athletes to erstwhile rivals, Hollywood A-listers and adjacent a US President.

Iron Mike has been backmost successful boxing with a fig of exhibitions implicit the years, but present he's stepping things up against Jake Paul.

The bout against a YouTuber 31 years his inferior volition beryllium his archetypal officially sanctioned combat since 2005.

In his prime, the likes of Arnold Schwarzenegger, Will Smith, Madonna, Pamela Anderson, Donald Trump and Jack Nicholson could each beryllium spotted ringside astatine Tyson's fights.

Here's the rundown of the boxer's all-star formed of personage BFFs.

Donald Trump

Mike Tyson and the US President-elect spell backmost galore years.

Trump was adjacent among the guests astatine Tyson's manic 30th day party.

In his publication 'Undisputed Truth', Tyson wrote of "spending a luck flying successful friends from each implicit the state and putting them each up successful a adjacent hotel".

They could not enactment successful his location due to the fact that the 19 bedrooms were reserved for each the "lady suitors" helium planned connected bedding.

Tyson wrote: "We had 13 antithetic chefs, each 1 cooking successful their ain kitchen.

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"Everyone from Oprah to Donald Trump to Jay-Z to thoroughfare pimps and their hos were there. There was a feline hand-rolling cigars.

"You entered the location connected an existent reddish carpet - erstwhile you got past the 40 large Fruit of Islam bodyguards stationed outside.

"I was truthful egomaniacal that I reserved the 19 bedrooms successful my location for girls who I wanted to slumber with.

"I told Crocodile, 'see each these girls? They're mine'."

And the boxer endorsed Trump successful some the 2016 and 2024 elections.

He told the Huffington Post successful 2016:  "He should beryllium president of the United States. Hell yeah, large time!"

And this year, helium went into much item connected the IT IS WHAT IT IS podcast, saying: "Trump is going to win.

"Yeah, it'd beryllium bully if helium wins, yeah. I person my reasons [for wanting him to win]... He is conscionable a bully man. Listen, I don't hold with each his s***.

"Nobody agrees with each my s***, but you know, they [are] bully people.

"No 1 is cleanable successful this world. Everybody got their s***, you know."

Dana White

Mike Tyson and Dana White person a communal person successful President-elect Trump, who they are some supporters of.

But Tyson has besides been precise supportive of the UFC boss' expanding engagement successful boxing and said helium expects White to get amended fights arranged.

He said: "That's going to beryllium the champion happening to hap to boxing conscionable similar UFC.

"If you're successful UFC and if anybody's booing the fight, you're not going to spot that guy. His adjacent combat is going to beryllium successful South Dakota somewhere. Only bully fights.

"If you don't person a bully fight, you ain't ne'er going to spot that feline again. Not similar boxing.

"'This guy's going to combat adjacent period again? We don't privation to spot that.'

"If immoderate fights stink, you're not backmost successful the UFC nary more. You're ne'er going to spot those guys again."

Novak Djokovic

Mike Tyson is simply a immense tennis instrumentality with his girl Milan a keen subordinate of the sport, which helium claims has changed his life.

And the boxer has revealed his favourite subordinate is Novak Djokovic.

He said: “Novak Djokovic is my favourite astatine the moment. If helium is OK, I truly similar to ticker him.

“He is my favourite due to the fact that the mode helium has travel backmost from wounded and beaten guys similar [Rafael] Nadal and [Roger] Federer is amazing. He is simply a existent fighter.”

The brace exchanged handshakes and took pictures astatine Indian Wells and Tyson is keen to be the Serb's matches whenever helium can.

Serena Williams

The 23-time Grand Slam victor is Tyson's 15-year-old girl Milan's favourite player.

In a representation successful 2016 with Serena and Milan helium wrote: "Milan connected the close and of people the large Serena Williams.

"Milan is superior astir tennis and is precise fortunate to get to walk precious moments Serena. Thank's Serena."

And the American, known for her powerfulness connected the tennis court, linked up with Iron Mike to enactment successful a brutal show with the pads.

Tyson wrote connected Instagram that Williams "has immoderate power".

And helium added: "I don’t privation to get successful the ringing with this GOAT @Serena Williams, overmuch emotion and respect."

Arnold Schwarzenegger

Following his ringside appearances, Tyson maintained his relationship with the Terminator prima turned politician of California.

In 2021, helium was invited to Schwarzenegger's LA mansion wherever the brace played chess and mini-golf together.

UFC prima Henry Cejudo, who joined the duo, captioned his pictures "Legends only".

Tupac

Mike Tyson and Tupac were adjacent friends with the rapper adjacent coming to sojourn him successful prison.

The boxing icon said: "I talked to him arsenic a young, shy kid. I went to prison, helium wrote maine a missive and came to spot me.

"That's however we became friends, we talked connected the telephone and built a narration I said to him, 'When I permission you'll beryllium coming in'.

"We were ever saying erstwhile we came retired of situation we would conquer the world, everyone would cognize our names that's what happened. But, you cognize [how the remainder went]."

And helium said that helium was adjacent meant to conscionable Tupac connected the nighttime helium was shot.

Tyson commented: "I was astatine home. I was expected to conscionable with him, past I heard the news. I was expected to articulation those guys, I wanted to bent retired with them."

He would past ne'er spot his pal again earlier helium died arsenic "they wouldn't fto anyone spot him" portion helium was successful hospital.

He continued: "I was home, I was successful my location erstwhile I recovered retired helium had died arsenic well. I was similar everyone else, it was truthful overwhelming, we mislaid idiosyncratic special."

Oprah Winfrey

Mike Tyson remains friends with Oprah, who made an quality astatine the infamous 30th day party.

He appeared connected the Oprah Winfrey amusement successful 2009 opening up connected the ups and downs of his beingness to date, from being bullied arsenic a kid to the decease of his four-year-old girl Exodus successful a household accident.

And connected the aforesaid show, helium made up with fierce rival Evander Holyfield.

When Oprah saw the movie of the interview, she was struck by Tyson's vulnerability.

She said: "I was truthful impressed with what you were capable to uncover astir yourself.

"It feels similar it's much than astir you - it truly is simply a survey successful humanity."

In 2021, Tyson would look with Oprah again connected Tom Brady's Let's Go! podcast.

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Evander Holyfield

Perhaps the astir improbable of Mike Tyson's personage friendships is with his biggest ever boxing rival.

For each his triumphs successful the ring, Iron Mike is possibly champion known for biting portion of Evander Holyfield's receptor disconnected successful their 2nd combat successful 1997.

But the 2 made up successful a associated quality connected Oprah.

Tyson said connected the show: "This is simply a beauteous guy, maine and this feline some travel from fundamentally the sewage, and we watched each different turn to go established and esteemed fighters, you cognize what I mean?"

"And I conscionable privation you to cognize it's been a pleasance passing done beingness being acquainted with you."

And 2 years agone they adjacent went into concern together, creating an edible cannabis merchandise successful the signifier of Holyfield's ear.

But helium didn't get connected with everyone...

In his memoir Undisputed Truth, Mike Tyson told an astonishing communicative astir Brad Pitt.

The histrion is claimed to person made the A-list of stupidity by sleeping with the feared erstwhile heavyweight champ's wife.

Tyson claimed that helium walked successful connected Pitt and his ex-wife Robin Givens having sex, with the Hollywood prima shouting "dude, don't deed me, don't deed me" erstwhile helium realised he'd been caught.

In the memo, the boxer wrote: "You had to spot the look connected his face. He looked similar helium was acceptable to person his past rites. He besides looked stoned retired of his gourd."

But Givens denied the claims successful an interrogation with Andy Cohen.

She said: "Pulling up successful the driveway? That part’s true. I thought helium said helium caught america successful bed.

"I didn’t work the book, but I was told helium said helium caught america successful bed, which ne'er happened. Never, ever, ever happened."