The Masked Singer Wiki

Pineapple is a masked celebrity on the first season of The Masked Singer.


The pineapple has a big head that wears sunglasses and also has a green-ish straw with a blue umbrella top. He wears a blue shirt with green & purple flowers. He also has a parrot on his shoulder. The pineapple also has a human body six pack. He also wears dark blue shorts with white. He has yellow feet and gloves along with black n' white flip flops.


Week Song Selection Result
2 "I Will Survive" by Gloria Gaynor ELIM


Week Clue
2 "Aloha, dudes. I become 'the Pineapple' because like me, they're fun, tropical, and go well with ham. Although I look happy now, I've gone through some dark times. After beating a life threatening disease, this OG has decided to take things as they come and never wipe the smile off my face. Though I've been in the public eye for decades, I've always dreamed of being a singer. So consider this a check off my bucket list. Life is short, man. You got to seize the day before your dreams go up in smoke."
Clue Answers
Cheech and Chong won a Grammy for best comedy recording in 1974.
Pineapple's mention of "up in smoke" was a clue to the 1978 film that made Cheech and Chong famous.
Pineapple's license plate number 52438T is Tommy's birthdate and the first letter of his name.
Other Clue Answers
Chong was targeted in the government’s Operation Pipe Dreams.
The Yin and Yang symbol was an homage to his Chinese heritage.

Final Guesses[]

Week Robin's Guess Jenny's Guess Ken's Guess Nicole's Guess
2 Sugar Ray Leonard Cheech Marin Jimmy Buffett Kid Rock


  • At 80 years old at the time of his unmasking, Pineapple is the oldest contestant on the American version of The Masked Singer.
  • Pineapple is the first contestant to have his identity guessed by one of the judges, but not as a final guess.
  • The Pineapple costume made a cameo in the Season 3 Wrap Up video. [1]
  • During Pineapple's only performance on a close-up, you can actually see his beard poke out once in a while.
  • Pineapple is the first Canadian to compete on the show.
  • Pineapple and Flower share the same birthday.
  • Pineapple and Frog share walk in songs, they are both Whatta Man by Salt N Pepa.
  • A back-up dancer wore the Pineapple mask during Octopus' performance of "Tutti Frutti" in season 6.
    • Coincidentally they were both first eliminated from their groups.





Interview Unmasked[]



External Links[]