In 2015 Jimmy won the Roastmasters Invitational (at JFL, Montreal) and he was back again in 2016. The Invitational was across 4 days, at L’Astral, and filmed by Comedy Central. See broadcast details here.

28^th July – Judges:

• David Spade
• Jeff Ross
• Kevin Hart

They watched 4 pairs of battlers:

• Jimmy Carr v Christi Chiello
• Sam Morril v Steve Rannazzisi
• Earl Skakel v Tom Ballard
• Sarah Tiana v Chris Cubas

Jimmy won his match and was through to Round 2. The voice is a bit of an issue but then she called him a “convicted criminal” for something that wasn’t illegal (he wasn’t charged OR convicted). So, it was all a bit weird and you can see from the comments how poorly she scored with comedy fans.

30^th July, final 8 – Judges:

• Jeff Ross
• Seth Rogan
• Jimmy Kimmel

The final 8 were paired:

• Jimmy Carr v Earl Skakel
• Mike Lawrence v Ralphie May
• Sarah Tiana v Sam Morril
• Tony Hinchcliffe v K. Trevor Wilson

Here’s a picture of the final 8 on stage with Brian Moses. Sam Morril to Jimmy’s left.

Earl was judged to have beaten Jimmy…because Seth Rogan and Jimmy Kimmel didn’t like that Jimmy was using a clipboard. Even though the judges said that he as “more consistently funny”.

There’s an overview of the rounds on Vulture.com.

Fair number of people tweeted / debated the battle on forums and made comments like

• Legend Jimmy Carr blows the roof off the place with perfect writing / delivery
• Jimmy Carr should have won that last battle. Earl was good, but not Jimmy Carr good!
• Jimmy Carr got robbed!
• I disagree completely with the last Roast Battle. Jimmy Carr completely destroyed Earl Skakel. Clipboard be damned.

I suppose comedy is subjective and it sounds like Kimmel / Rogan didn’t like it.

Skakel had gone on stage shirtless and this Earl Skakel interview in Interrobang mentions that Jimmy had said off camera “it’s like this guy’s trying to make it a wrestling match”. Which suggests to me that they had never met before – hence Jimmy needing to have his jokes written down.

Earl posted this clip of them trash talking each other, before they battled.

Earl has posted something similar to this (2023-12) a couple of times now…

But followed up with the below – so clearly, no hard feelings.

And finally…Mike Lawrence eventually went on to win.