10 Times Drag Race Queens Cracked RuPaul Up in Comedy Challenges

#10: Jessica Wild’s Roast

All Stars 8

Judge Carson Kressley got the roast treatment in the eighth installment of “All Stars.” Season 2 queen Jessica Wild rose to the occasion, and had Ru and the entire room busting a gut with her outrageous takedowns. She skewered Kressley’s talent, or lack thereof, and his career choices, honing in on his run with “Dancing with the Stars.” Jessica’s over-enunciation and rhythm made her set so great. RuPaul’s guffaws rocketed through the soundstage. Every new dig at her co-star tickled her so much that it almost makes you wonder if she’s enjoying this a little too much.

#9: Alaska’s Roast

Season 5

The Pittsburgh queen had the daunting task of opening “Drag Race’s” roast challenge. Needless to say, the stakes were high. RuPaul wasn’t just judging. She was the guest of honor, so the queens had to carefully toe the line between funny and insulting. Alaska was smart. She started with the other judges first and worked her way up. But by the time she got to RuPaul, mostly taking aim at her age, the host was primed and ready. It’s clear why she was a frontrunner this season. Alaska handled the stage like a seasoned pro, and no one was laughing harder than Ru.

#8: Bianca Del Rio’s Stand-up

Season 6

She was the season’s comedy queen. This was the moment in season 6 – it was either going to make Bianca Del Rio or break her. Bianca put it quite eloquently herself. As soon as she called the gathered audience of old folks the cast of “Cocoon,” RuPaul was hooked. Mostly mining her own ethnicity for humor, Bianca’s set was as rotten as expected. It bowled the host over. Although she does take aim at the judges, she seems to leave RuPaul out of her jokes. After all, she knows who’s writing that hundred thousand dollar check.

#7: Jimbo’s Roast

All Stars 8

The “Canada’s Drag Race” contestant decided to resurrect one of RuPaul’s old friends for the Carson Kressley Roast. In character as Joan Rivers, Jimbo didn’t just roast Kressley. She incinerated him, RuPaul, Michelle Visage, and her fellow contestants. And she did it all in the voice of the lovable queen of mean. The jokes were vulgar, the timing was impeccable, and Jimbo had to pause more than once to let Ru finish laughing. A devoted fan of the late comic, RuPaul called the performance an honor to watch. She should know. She actually knew Joan Rivers.

#6: Kandy Muse’s Roast

Season 13

Some of this queen’s set could have used some finessing, but the priority is always to make RuPaul laugh. And Kandy Muse had the host in stitches the entire time. Her jokes about the Miss Congeniality winners were nasty, but it was what she had to say about Ru herself that really got her. The quip about “Jurassic Park” bringing back memories was fabulous. However, it was the one-two punch of that joke and the one about what happened when Kandy told Ru to act her age that really sealed it. That bizarre gesture where she posed like a corpse? It had us cackling and making memes all over the internet, but it had Ru literally gasping for air.

#5: Jujubee’s Snatch Game of Love

All Stars 5

This repeat finalist has made RuPaul laugh more than any other contestant. A lot of that has to do with just how many seasons she’s been on. But playing opposite Shea Couleé’s weirdly feminist version of Flavor Flav, Jujubee brought the weirdness to her interpretation of Eartha Kitt. Jujubee used the screen and stage icon’s gravitas to make even the most mundane things sound incredibly grand. One particular moment, that was immediately memed to death, was her answer to a question about how to keep her man warm. She sensually described turning up the thermostat, and RuPaul absolutely lost it.

#4: Trinity K. Bonét’s Stand-up

Season 6

This was the big surprise of the season’s comedy challenge. Trinity K. Bonét’s amazing stand-up set was a turning point in her “Drag Race” journey. Things weren’t looking promising at first. But Trinity was able to mine the hardships she faced in her childhood for all the humor she could. If Ru’s reaction is any indication, there was a lot of humor to be found there. Talking about her grandmother’s light bill and the plight of having no food really just got the host right together. RuPaul wasn’t just crying with laughter. She cried when it was over because she was so proud of Trinity.

#3: Alyssa Edwards’ Snatch Game

All Stars 2

There are so many “Drag Race” queens at this point that it’s kind of inevitable that Ru would have favorites. Alyssa Edwards is just one of those performers who can do anything and get a laugh out of her. Her Joan Crawford impersonation, clearly inspired by Faye Dunaway in “Mommie Dearest,” is really just a collection of lines from the movie. But Alyssa is so singular a performer that it doesn’t matter. It also doesn’t even matter that her answers don’t really make much sense, but Ru is coming apart at the seams from laughing so hard.

#2: Jinkx Monsoon’s Roast

All Stars 7

If this two-time winner is in the room, you’re bound to hear RuPaul cackling somewhere. All the way back to season 5, Jinkx Monsoon knew exactly where to find Mama Ru’s funny bone. Her original roast was a huge highlight, and her brilliant Snatch Game as Judy Garland saw RuPaul nearly falling over in a giggle fit. But we’d say she cracked up even harder at Jinkx’s contribution to the all-winners roast. In fact, from the very first joke, RuPaul was actually screaming. And then she just didn’t stop. We’re honestly wondering how she had a voice or the lung capacity to keep laughing at the other queens after Jinkx’s set.

#1: Coco Montrese’s Roast

Season 5

The RuPaul Roast was a triumph for this lip sync assassin. Coco Montrese created the character of RuPaul’s long-lost cousin who doesn’t get out much. It’s a hilarious conceit that pays off. Even Ru looks worried about what to expect. But she immediately sets the tone, being overly-familiar with the host and immediately taking apart her look out of drag. One joke about Hurricane Katrina had RuPaul laughing so hard, she started waving her hand in the air like she wanted Coco to stop before she hurt herself. It was a well-deserved win for Coco, especially since she was up against some stiff competition. But the fact is we’ve rarely seen Ru crack up quite this hard.

Did these moments make you laugh as hard as Ru? Tell us in the comments.