Top 20 RuPaul's Drag Race Roast Win & Fails

The all winners edition of “All Stars” saw some stiff competition. Jaida Essence Hall is not necessarily a natural comedian, but her set started strong and the writing wasn’t bad at all. Then, as she began stumbling over her words, she lost her rhythm. It became clear she was struggling. Although it was funny to watch her acknowledge she wasn’t doing well, it was a shame to watch some pretty decent jokes go to waste under some shoddy delivery. Still, it taught us one thing. If you must fall on your face, do it as gracefully as possible.

She may have been the sole survivor of season 14’s Snatch Game, but DeJa Skye went down in flames at the Ross Mathews Roast. Instead of laughs, most of her cutting humor got guffaws and scandalized “oh my Gods”. Even her best jokes she couldn’t help but undercut with an unnecessary comment. It was clear from the reactions that the bulk of her insults toward Michelle Visage and Ross Mathews weren’t going over well with anyone either. She saved face with her last joke, but when your best quip is literally your exit line, you know you didn’t do well.

Even though she landed one of the night’s best jokes, Olivia Lux couldn’t overcome a weak set and a cloying onstage persona while roasting previous Miss Congeniality winners. Olivia’s smiley-faced, wide-eyed persona grew tired pretty fast. Indeed, her stumbling and breathy airhead routine didn’t do too much to lift some subpar material either. It could be that Olivia’s just too nice for a roast. Yet some of her jabs would suggest she has the potential to get down and dirty with the best of them. Indeed, the shade was present. What was missing was the proper stage presence and an ability to truly land the jokes.

RuPaul’s old friend Lady Bunny has been one of the show’s favorite punching bags over the years. So the “All Stars” 4 cast was going to need more than simple old age jokes to make us laugh. Naomi Smalls, however, seemingly did not get the message. Her jokes were sweaty, to say the least. She clearly wasn’t comfortable doing standup, and her nervous laughter just highlighted the lack of positive crowd response after each punchline. Sadly, the funniest thing about Naomi’s roast was Monét X Change’s commentary, and that was because it just pointed out the obvious.

Valentina has unleashed some great reads in the past, but she crashed and burned trying to roast legendary drag queen Lady Bunny. It didn't help either that she took 30 seconds to set up her first punch line, only to offer an underwhelming visual gag. Though Valentina's attempt at mocking her mask scandal was admirable, it was far too drawn out and simple. Her bizarrely sexual jokes also focused too much on pushing the envelope rather than saying something witty. Given that the commentary about Valentina's stand-up was more entertaining than her actual material, this roast was painful to watch.

For Michelle Visage's roast, Trinity The Tuck spiced up her comedy with a colorful ranch girl persona. Despite some snappy farm humor however, many of her jokes were just far too lengthy. Trinity's continuous stream of childish bathroom gags lacked depth too, which resulted in plenty of silent audience responses. And though they brought a side-splitting Caitlyn Jenner to the 'All Stars' Snatch Game, the constant joke explanations at the roast of Lady Bunny hurt the set. Trinity's stiff execution was dreadful enough that she actually roasted herself in response as well. With this kind of poor writing, Trinity's roasts felt much longer than the short airtime they were given. However, Trinity more than redeemed themself in the All Stars 7 roast.

Alaska left everyone with a hard act to follow at RuPaul's roast, but Roxxxy Andrews still managed to read her as a discount Sharon Needles. Sadly, Roxxxy's nerves ruined the rest of her routine as she stumbled awkwardly through otherwise decent material. Even a quick jab at Ru's age sounded mean thanks to her dry inflection. Roxxxy stopped so many times trying to insult Michelle that she deflated the impact of her wordplay too. Thankfully she was cut-off quickly though, as the editors were really emphasizing her mistakes through the audience. But Roxxxy's clunky performance was all the more agonizing since most of her good jokes couldn't survive her delivery.

Despite her usually hilarious antics in the workroom, Alyssa Edward's sharp sense of humor fell flat at the roast of RuPaul. Though she threw in some clever wordplay about cracks, her sloppy delivery hurt every joke she had. Edward's attempt to call the competition trashy also felt obvious and a little undercooked for where she could've taken the idea. Some smart puns and digs at Santino Rice came out half-baked as well, and showed potential for a great routine that was never refined. While the editing definitely played into how bad Alyssa's set appeared, her lackluster writing was what earned her a spot in the bottom two that week.

Tasteless jokes got particularly out of hand during Michelle Visage's roast, but they only reflected poorly on the people saying them. Farrah Moan's detail-heavy read on Michelle's fame just stated facts maliciously and didn't have a true punch-line. After Farrah's tactless quip about sexual favors however, it was satisfying to watch Visage grimace in contempt. Alexis Michelle on the other hand insulted Fortune Feimster's career without any sort of comedic twist. Visage was also the only one laughing at Alexis's predictable humor. Plus, the watersports gag was too obscure for the judge, let alone for viewers. This all contributed to closing the roast on a sour note, and understandably landed Farrah and Alexis in the bottom two.

In one of the most spectacular roast fails in herstory, season 13’s kooky fashion icon, Utica Queen, experienced the gamut of the “Drag Race” standup comedy experience. She almost landed at least one joke, bombed so hard the next studio heard it, got dressed down by one of the judges, and the host even gave her the finger. It’s kind of a wonder how bad she was considering how incisive and brazen some of the jokes sounded on paper. But they were too vulgar, too underwritten, and too bizarre to ever have a chance. Utica’s best moments came courtesy of guest judge Loni Love and RuPaul, who both had the perfect response to her remarks about them.

Opening a comedy show is no small thing. Bosco, however, had a lot of material to work with… herself. She managed to turn her weak points in the competition into great fodder for a string of one-liners about how often she’s been told to go home. Because if you can’t roast yourself, how are you gonna roast somebody else? But Bosco’s ingenuity didn’t stop there. She got off several great digs at her fellow contestants before turning on the judges. Even her “RuPaul is so old” line manages to be one of the most unique versions of that joke ever told on that stage.

There is something so naturally funny about Jessica Wild. When it came time to do the Carson Kressley roast, she didn’t make the same mistake as many queens before her. Rather than just relying on her natural charisma and hoping for the best, she brought an incredible and surprising set of jokes. Adding in clever turns of phrase and that iconic Jessica delivery only she can nail just made the whole thing that much funnier. Taking aim at Carson Kressley’s charisma, uniqueness, nerve, and alleged talent, she consistently made the room erupt with laughter. Jessica’s punchlines were so unexpected, mostly because no one is quite like her.

Kandy Muse’s set may not have had the polish, but that’s what’s so great about her. Her jokes were great, and even the ones that were a little shaky were saved by her commitment to the bit. Using her amazingly husky voice to drive her punchlines home, Kandy was a natural on the stage. Guest judge Loni Love almost seemed apprehensive when the queen set her sights on her. When they’re laughing but also scared for their turn, that’s when you know you’re killing a roast. What really drove it home was Kandy’s gestures. That wild coffin pose she struck on her last joke was instantly memeable.

Considering Jinkx Monsoon finally came alive as one of season 5’s most gifted comedians, this “RuPaul Roast” performance was almost like a victory lap. The queen scored right from the start, with a clever and crass pun. That energy was maintained throughout the entire set, as Jinkx notably took aim at Michelle Visage and RuPaul in spectacular fashion. Whip-smart, confident, and concise, the routine was smart without sacrificing the vulgarity we’ve come to know and love. The star’s comedic stylings haven’t gotten any less impressive with time, either. When Monsoon returned for the all winners season, the zingers were still ultra hot.

For the first ever 'Drag Race' roast, Alaska set the tone by comically insulting Leslie Jordan and Michelle Visage at the same time. And her endless riffs on RuPaul's age were wacky enough to have Ru herself screeching. From disasters to some graphic medical issues and more, she brought laughably great material on a topic that's usually overdone. In her critiques on RuPaul's career achievements, Alaska's snarky tone gave her comedy an edge many queens lacked. This also allowed her to fire off particularly harsh words at Roxxxy Andrews while she was heading off the stage. This comfort to leave no stone unturned in her routine assured that Alaska never gave audiences a dull moment.

While prop comedy can be tacky at times, Monét X Change's glasses provided a goofy and lighthearted tone for her Lady Bunny reads. Though mentioning Beyoncé would seem like a compliment, Monét actually invoked Knowles-Carter’s name to riff on Lady Bunny's appearance. Monét's ancient bible references wittily ripped into Lady Bunny's age too. However it was her detailed story about eating other queens that left everyone in stitches. In the wrong hands, these quips could’ve crossed a line and come across and unnecessarily mean. Yet Monet struck a friendly yet zany tone throughout the roast that kept people laughing, and more than lived up to her reputation as a comedy queen.

To capitalize on the funeral theme of Lady Bunny's roast, Manila Luzon made a dramatically gloomy entrance. Her excessive recoil upon smelling Bunny however, was completely unexpected and hysterical. Manila touched on death too, just to comically read Lady Bunny for eating too much. And just when her jokes got incredibly saucy, she threw in another twist about the dearly departed's appetite. It was all these creative subversions of funeral clichés that allowed Luzon to stand out and nab a spot in the top two as well. By getting Lady Bunny laughing and simultaneously burning her fellow queens, Manila had a roast worthy of an all star.

This iconic queen decided that the only way to properly do insult comedy was in character as one of the most famous insult comics of all time. Reviving her winning Snatch Game impersonation from the first season of “Canada’s Drag Race,” she was on fire from start to finish. Jimbo’s Joan Rivers was as quick-witted and vicious as the late woman herself. This kind of take-no-prisoners approach could have easily come off as awkward. But the strength of the jokes and Jimbo’s characterization of Rivers were so spot-on that it almost seemed as if the comic had been revived for one last gig.

This lip sync assassin strayed far from her comfort zone for the show’s first ever roast, and it was a gamble that paid off big time. Coco Montrese decided to perform in character as RuPaul’s fictional cousin. She found humor in those people who try to bring you back down to earth because they knew you before you were big. Nothing was off limits when it came to Ru either, with Coco taking aim at the host’s appearance and pants. Needless to say, RuPaul was gasping for air. It was a real turning point for Coco in the competition, earning her her first main challenge win of the season and a place among the best roasters in “Drag Race” herstory.

There was a loving quality to Peppermint's voice at Michelle Visage's roast, which gave more punch to all the shade she dished out. Peppermint used this warm energy to praise Ross Matthews in the most backhanded way she could. She also questioned Michelle's outrageous negativity for a side-splitting deep cut on her book. Peppermint's research allowed her to deliver long-form jokes that actually stuck the landing, while also touching on subjects that her competitors missed. However it was her genius Destiny's Child comparison that had everyone laughing the longest. This fierce comedic talent and her great timing helped Peppermint win the roast challenge and showed audiences she had the talent to go all the way.

Which of these roasts had you clutching your pearls? Once the shade clears, leave us a comment.