Who Won Miss Pineapple 2021?

There was a space ship. A children’s cartoon song. And…a murder?! The 2021 Miss Pineapple Pageant presented by Falcon|NakedSword to benefit Pineapple Support is in the books! Which gay porn star came out on top? (And which one was poisoned?!)

Following the highly successful inaugural pageant in 2020, Miss Pineapple returned on Sunday (FREE on Weekends at NakedSword!) with gay porn stars galore, special guests, messages of strength, and even the birth of a baby! Acclaimed director Marc MacNamara (who flashed his animal underwear) and Sister Roma returned as hosts, joined by celebrity guest judges Wesley Woods (the 2019 GayVN Performer of the Year) and his gal pal Silvia Saige; Falcon|NakedSword Superstar Exclusive Max Konnor (the 2021 XBIZ Gay Performer of the Year); and RuPaul’s Drag Race and All-Stars fan favorite Detox!

The four contestants were joined by 2020 winner Dakota Payne (aka Gemini Dai) in special recorded performances and live interviews. Who won?!

Jack Hunter (Tara Dactyl)
Jack performed to a medley of “True Colors” by Zedd, “Notorious: by  The Saturdays and, um, “I’m a Pterodactyl” from a children’s cartoon by Howdytoons (say wha?!). There was a spaceship. Sex with aliens. And the birth of a baby (although by the looks of it, that baby should be coming out of her mouth). The performer (looking cute in his pineapple headdress) noted it was the “origin of Tara Dactyl from conception to birth to beyond the stars,” adding later that having faced depression and mental health issues all his life, he was happy to spread the word for the services of Pineapple Support.

Adrian Hart (Serenity Dai)
Adrian—the drag daughter of Dakota’s Gemini Dai—performed to a Demi Lovato medley (“Dancing with the Devil,” “Sober” and “I Love Me”) in his very first drag appearance, noting that he used the time during the pandemic to become sober by cutting out alcohol. There was some amazing outfits and a special guest dancer!

Jay Seabrook (Sinna Moon)
Jay performed to “Passion and Pain Taste the Same When I’m Weak” by Tove Lo, and noted that it was tough being his skin color growing up in Venezuela. He adopted his drag name as a nod to his “cinnamon skin” and said that the performances in the 2020 Miss Pineapple show inspired him. His passion came through in his commitment to the lyrics (that was serious emotion, y’all!).

Liam Riley (Bambi Wadley)
Liam performed to “Dead” by Madison Beer, and he wasn’t kidding: “You say you can’t live without me, so why aren’t you dead yet?” crooned Bambi to boyfriend Liam, who found himself drinking a poisoned glass of red wine as the diva got her revenge. (And looked amazing…especially those nails!)

Dakota Payne (Gemini Dai)
In a special appearance before surrendering his crown, Dakota performed to a Des’ree medley of “I’m Kissing You” and “You Gotta Be.” And good look not getting emotional during the first half, which was dedicated “To those we love, to those we lost” and pulled at the heartstrings. The latter half got cheerier as Dakota was joined by a few dancers (is that Adrian again?!) and hit the streets to show off their pride.

The judges loved all of the performances…at least I think they did. Any time they were on screen and talking, I was too distracted by Max Konnor’s biceps to remember anything…

At the end of the show, the contestants spoke to the important message that Pineapple Support champions, and Detox had the honor of announcing the winner…Jay Seabrook! Congrats to Jay! To make a donation visit PineappleSupport.org, which provides free and subsidized mental health services to the adult industry.