Kyle Sandilands gets roasted by comedian Jim Jefferies on his 50th birthday

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Radio host Kyle Sandilands was roasted by his favorite comedian on Thursday as he celebrated his milestone 50th birthday.

Jim Jefferies got a free hand on The Kyle and Jackie O Show to ridicule the shock jock about his weight, ill health and habit of dating younger women.

While Kyle notoriously loves to be mocked in the air, he made an exception for Jim, 44, because he’s such a fan of his comedy.

Taking it on the chin: Radio host Kyle Sandilands was roasted by his favorite comedian on Thursday as he celebrated his milestone 50th birthday

Kyle’s co-host Jackie ‘O’ Henderson hosted the roast, which Jim performed via Zoom from his quarantine hotel after recently arriving in Australia for a tour.

‘This is my first time doing it. I’ve written about five jokes, so let’s see how they go,” he said before starting his routine.

Jim then began, “Happy Birthday Kyle. Fifty years old. I’d love to do your sixtieth, but I doubt we’ll make it.’

Roast: Jim Jefferies was given free rein on The Kyle and Jackie O Show to ridicule the shock jock over his weight, ill health and habit of dating younger women

Roast: Jim Jefferies was given free rein on The Kyle and Jackie O Show to ridicule the shock jock over his weight, ill health and habit of dating younger women

He added: “I met you once on one of my shows and I always thought, ‘It would be nice to be friends with Kyle, but he just lives too far away in Australia.’ And then I found out you’ve lived most of your life in LA, two miles from my house.

“It’s still too damn far away.”

Jim then told a joke about Kyle’s years as a homeless teenager in Brisbane.

‘F**king hell, you couldn’t be homeless anymore. You couldn’t live in a gutter unless it was a fucking four-lane highway,” he said.

“Imagine this fat c**t showing up in a soup kitchen.”

Fan: While Kyle notoriously dislikes being mocked in the air, he made an exception for Jim, 44, because he's such a fan of his comedy

Fan: While Kyle notoriously dislikes being mocked in the air, he made an exception for Jim, 44, because he’s such a fan of his comedy

After this, the roast took an unexpected turn when Jim turned his attention to Jackie.

“You have a lot in common, Jackie O, with the original Jackie O,” he said.

This was a reference to Jackie Kennedy, wife of assassinated US President John F. Kennedy, who later became known as Jackie Onassis – shortened to Jackie O in the tabloids – after her marriage to Greek shipping magnate Aristotle Onassis.

Jim continued, “You sit next to important men and you contribute nothing.”

Jackie, 46, was furious at the comment, yelling, “What the f**k?! This isn’t about me, Jim. This is a roast on Kyle.”

But he wasn’t done there, as Jim continued, “So, Kyle, I’ve found you’ve been the most hated celebrity in Australia six times.

“And that’s twice after Rolf Harris was convicted of being a pedophile. Imagine losing a popularity contest to a guy who dates younger women than you!’

Kyle laughed so hard he couldn’t be mad, even admitting, “All correct so far too. Don’t even lie, this guy.’

Jim ended his routine and continued, “Some people have called you a sugar daddy, but with your size, it should be a diabetes daddy.”

Without arguing, Kyle laughed so hard he couldn't be mad, even admitting, “All correct, too, so far.  Don't even lie, this guy'

Without arguing, Kyle laughed so hard he couldn’t be mad, even admitting, “All correct, too, so far. Don’t even lie, this guy’

“I deserve it,” admitted Kyle, who has made no secret of his weight struggle over the years.

Kyle’s positive response to the roast was surprising, as he’s actually quite thin-skinned, despite his brash on-air persona.

Several years ago, he said he would never do ABC’s Hard Chat with Tom Gleeson because he didn’t like being mocked.

However, it seems like he wants to make an exception for a comedian he really likes.

Picking Favorites: Several years ago, Kyle said he would never do ABC's Hard Chat with Tom Gleeson (right, with The Veronicas) because he didn't like the idea of ​​being mocked.  However, it looks like he's willing to make an exception for a comedian he really likes

Picking Favorites: Several years ago, Kyle said he would never do ABC’s Hard Chat with Tom Gleeson (right, with The Veronicas) because he didn’t like the idea of ​​being mocked. However, it looks like he’s willing to make an exception for a comedian he really likes

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