Rudy Giuliani’s ‘Masked Singer’ Turn Is the Show’s Worst Decision Yet (Column)

Perhaps the only gratifying thing about Rudy Giuliani’s appearance on “The Masked Singer” is that the element of surprise the show’s producers craved was ruined in advance.

Wednesday night’s episode of “The Masked Singer” saw former New York City mayor and lawyer for former President Donald Trump revealed as the Jack in the Box. Fitting his costume, the disguised Giuliani explosively popped out of his captivity to perform George Thorogood and the Destroyers’ “Bad to the Bone” after a dancer turned his crank, to squeals of delight from the show’s audience and judges. There was little suggestion of who he was — indeed, the package of hints the show provides focused on the random and tangential fact that Giuliani has performed weddings with frequency. His reveal at the end of the show — a fact that had been already been known to the public after Deadline reported in February on multiple judges’ walking off set — was treated as a dark surprise by Ken Jeong and Robin Thicke, the judges who had apparently been angry with the casting of Giuliani.

The mood seemed dour post-reveal, with Jeong outright glowering and crossing his arms, and eventually walking off during Giuliani’s reprise performance. “It surprises us all that you’re here on ‘The Masked Singer,’” the usually ebullient host Nick Cannon said flatly. No kidding. (The judges’ guesses as to Giuliani’s identity had been Robert Duvall, Elon Musk, and Joe Pesci, all more credibly part of the world of entertainment.) While it’s not unprecedented for this show and others like it to feature political figures, Giuliani’s role in the attempt to overturn the results of the 2020 presidential election would certainly seem disqualifying.

It’s a frustrating turn for a show that has been, since its 2019 launch, something of a unifying force in the pop-culture landscape. Sure, former vice-presidential candidate Sarah Palin appeared in the past, and her presence on the show might have been more subject to debate had the world been steadier. Palin’s appearance, performing “Baby Got Back,” came in a March 2020 episode that is remembered, if at all, for appearing the same night as Tom Hanks announcing his COVID-19 diagnosis and the NBA postponing its season.

But if Palin’s rhetoric (prior to her current run for Congress in Alaska) presaged our current, dangerous political moment, Giuliani’s is utterly of it. As the attorney for Trump in the aftermath of the 2020 election, which Trump lost, Giuliani asked a Republican prosecutor in Michigan to hand over voting machines to the Trump campaign. He had his law license suspended in the state of New York for his “demonstrably false and misleading statements” about the outcome of the election. And he worked to place illegitimate electors in place to cast votes on behalf of seven states Trump lost, all in an effort to subvert the will of the people.

Even those who were Giuliani skeptics or critics in past eras of his career can acknowledge that this is a particularly sad ending for the mayor who led New York City on September 11, 2001 — although Giuliani attempted to put a positive spin on his appearance by saying it was intended to inspire his baby granddaughter to take risks. But “The Masked Singer” isn’t drafting off of his status as an admired citizen, any more than it booked Palin because of what she accomplished in office as the governor of Alaska. The show is asking its audience to thrill to Giuliani’s aura of scandal and intrigue. Indeed, why else place him on the so-called “Team Bad” on the season-long conceit of “The Good, the Bad, and the Cuddly,” or have him stumble through talk-singing the lyrics of “Bad to the Bone”? The show wants us to be appalled. (Judge Nicole Scherzinger, a perennially smooth and assured presence, refused to play along, asking Giuliani if it was true he’d performed many weddings in his life — skating right past his aura of scandal. “Your family’s gonna love it!,” she said, breezily.)

This makes the onetime booking of former Trump press secretary Sean Spicer on ABC’s “Dancing With the Stars” — a decision that show’s host criticized — look like a mild misjudgment. (In tepid fairness to Fox, which shares a parent company with Fox News, casting Trump administration personalities for redemptive moments has indeed happened elsewhere on the dial.) Spicer told untruths from the briefing room podium; Giuliani put his reputation and his very best effort behind actually overturning an election. There’s nothing cute or funny about it, nor anything worth celebrating as a comeback story. “The Masked Singer” is a show that tends to find in the worst sort of performances a sort of human redemption, and fun freewheelingness that allows us to be impressed a non-singer tried; Giuliani’s humiliation ought to be met with the public denying him any more attention after today.

It is frustrating to be reminded that for some, everything is a joke; the casting of Giuliani here seems less an ideological statement of his worthiness and more than his potential resurfacing would be as quirky and interesting as a comeback for the 1990s chanteuse Jewel, who won the last “Masked Singer.” Treating Giuliani as a plaything for our culture, albeit one who has made some controversial choices, is not a matter of policy disagreement, or of being a bit too grave about the lighter side of the news. Fox gave time and attention to a powerful figure who would have, if given his way, put the last nail in the coffin of democracy in this country. One hopes that Fox will learn from this. But one suspects, too, that the attention this incident brought to an aging franchise — up to and including this article — means that they’ll be happy with the result.

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