From Rudy Giuliani to Tony Hawk — 6 ‘Masked Singer’ moments that flipped audience’s expectations

‘The Masked Singer’ is where the audience uses all of their brains to guess the identity, but were you able to guess these legends?
PUBLISHED JUN 28, 2025
(L-R) Lil Wayne, Tony Hawke, Kevin Hart (Cover Image Source: (L) YouTube | The Masked Singer; (C) YouTube | Mr. Diricio; (R) YouTube | yuval)
(L-R) Lil Wayne, Tony Hawke, Kevin Hart (Cover Image Source: (L) YouTube | The Masked Singer; (C) YouTube | Mr. Diricio; (R) YouTube | yuval)

The Masked Singer’ remains one of the most popular singing competition shows. Its biggest appeal lies in the dramatic unmaskings that leave fans and judges stunned every time. Since its inception, the show has kept viewers guessing, only to later leave them completely surprised. 

1. Rudy Giuliani as Jack in the Box 



 

Let’s begin with the unmasking that made a judge walk off the set, and not for any good reason. Rudy Giuliani was seen on Season 7 of ‘The Masked Singer’ dressed as Jack in the Box. Judges excitedly guessed names like Robert Duvall, Joe Pesci, Al Roker, and even Elon Musk. But when he was revealed as Donald Trump’s controversial former attorney, Ken Jeong walked off the set. While his reveal was a shocking one to the panelists, it somehow did not hold a similar emotion for the viewers, as Giuliani's unmasking was already leaked before the season aired.

2. Kevin Hart as Book



 

Who doesn't love Kevin Hart? Dressed as Book in Season 11, Hart charmed the audience when he unmasked himself. Turns out, his performance was a prank on his longtime friend, host Nick Cannon. During Hart's stint on the show, the judges seemingly knew who was under the mask, as Robin Thicke was seen controlling his laugh. Nevertheless, both the audience and judges were left in tears of laughter after the ‘Get Hard’ actor revealed himself. As per Entertainment Weekly, prior to the season, a spokesperson for Fox teased, "The first unmasking in the premiere is absolutely insane; you cannot miss it.”

3. Lil Wayne as Robot



 

Another fan favorite who joined the show was rapper Lil Wayne. He appeared in Season 3 of the show. Many guessed his identity early on, as he showcased his signature vocal style. However, when he pulled off the mask, the rapper’s revelation became so startling that Thicke stated, "This is the most shocked I've ever been on this show." As per the rapper, he has been a fan of the show since the "first episode, because the first episode, when it came on, I knew it was T-Pain."

4. Mickey Rourke as Gremlin



 

Actor Mickey Rourke, known for roles in ‘The Wrestler’ and ‘Iron Man 2,’ also joined the show. He appeared in Season 4 dressed as the Gremlin. However, it was his only performance. The former boxer eliminated himself, saying the costume was too hot, and pulled off his mask mid-show. On the show, he sang Ben E. King's "Stand By Me" as a tribute to his late friend Willy Deviller. 

5. Billie Jean King as Royal Hen



 

One of the more surprising sports star reveals came when Billie Jean King appeared on the show. The tennis legend appeared in Season 10 as the Royal Hen. While her revelation stunned everyone, Jeong had almost guessed her identity. She performed Elton John’s 'Philadelphia Freedom,' a song originally written for her.

6. Tony Hawk as Elephant



 

One unforgettable moment was when skateboarding legend Tony Hawk appeared on ‘The Masked Singer.’ Dressed as an Elephant, Tony Hawk appeared on Season 3 of the show. Hawk was the first one from Group B to go home, and when he removed his mask, all of the die-hard viewers were simply shocked to witness the great personality on their TV screen. Talking to Gold Derby in an interview after the unmasking, the skateboarding legend stated, "I had one more song in me, but I didn't want to go much further."

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