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‘Michael Bolton’s Big Sexy Valentine’s Day Special’ Is Almost A Wonderful Thing

By  · Published on February 13th, 2017

Michael Bolton’s surreal seduction suffers from piecemeal writing.

You wouldn’t think there’d be much to something called Michael Bolton’s Big, Sexy Valentine’s Day Special, right? Certainly not a UHF-style telethon and the legal invocation of The Santa Clause. But with the twin comic powers of Comedy Bang Bang and The Lonely Island behind him, Michael Bolton runs one hell of a complicated show.

Bolton, an executive producer on the show, has a great sense of humor and performs all his bits (including the songs) with barely-contained glee. He’s really a fan of these guys. So when he rebuffs Adam Scott’s (who’s wearing the most distressed Springsteen concert tee to ever have its screen-printed letters fade) desperate party invitations to Las Vegas, Reno, and eventually Cincinnati, his explanation that it’s Valentine’s Day – and only ten months ’til Christmas – readies us for energetic fun.

Bolton’s year-round tan and blinding white teeth embody the kind of narcissism you’d normally associate with traditional holiday-pushing, money-grubbing songs, not parodies. The immediate connection, especially when Santa shows up, is to Bill Nighy’s rock star in Love Actually. They’re both aging pop icons embracing the weird flip side of their pleasant veneers, subverting expectations while still nestling into the genre that made their careers.

Santa’s absurd request for Bolton to make a Valentine’s Day Special (so there’ll be more babies to give the North Pole’s surplus presents) interrupts an opening tune with the same production values and sunny disposition as the Awesometown Theme Song. They’re not hiding that they’re on a set, it just adds to the weird charm.

Bolton outlines the day’s proceedings, giving a tour of the sexually-optimized bedroom in which the special takes place that fits snugly somewhere between IKEA and Fifty Shades of Grey. The same speaking-followed-by-emphasis-singing that Bolton did to great success in his debut with The Lonely Island boys, “Jack Sparrow” (of which there’s a romantic reprise at the end of the special), underlines the home’s erotic aspects (like a bear pelt to remind us that we’re still alive and capable of making love).

Bolton changes into some schmaltzy outfits, including an entwined-heart sweater and a gold leaf-flecked blazer, that look like something a particularly out-of-touch sultan would wear to a nightclub. His deadpan intermingled with suave tunes treats us as both star and guide through a series of Crazy Ex-Girlfriend-esque skit/songs separated by SNL commercial break stings of him gesturing sexily at the camera, sometimes accompanied by a forest animal.

The skits themselves are mostly funny, some just feel out of place in this sex-slathered bricolage of comic approaches.

Sarah Silverman and Randall Park’s increasingly dirty Sonny & Cher riff benefits from the “It’s a Small World (After All)”-like choreography, bouncing up and down like Oompa Loompas, and Bolton’s continued heckling (“You’ve sung about pubes twice!”). Andy Samberg’s Kenny G is hilariously villainous despite Bolton and G being friends (G introduced Bolton and Nicollette Sheridan who would become Bolton’s fiancee) – things seem to have ended badly when Bolton chopped off his long locks. Their sultry “Dueling Banjos” ends with a surprise guest and some delicious non sequiturs.

A group of special-crashing punks are soothed by Bob Seger’s “Old Time Rock and Roll” as Bolton dons a sparkly double rider motorcycle jacket that serves as an echo of the punker’s own – only the lights can’t stop winking off Bolton’s. The corny oddball number is interrupted by a flashback cut to choreography rehearsal, granting the song the kind of imaginative fun available to a creation with such talent and surprise behind it. Netflix specials are still the Wild West of the TV/movie conversation and Michael Bolton wants to go full Westworld. In this particular bit, a Tom Cruise in Tropic Thunder-channeling Michael Sheen screams and chomps his cigarettes with the right amount of weird edge to take advantage of the already strange, heightened, no-rules proceedings.

However, some bits play a bit too safe, or at least too familiar.

Fred Armisen’s bone dry chocolatier skit is too Portlandiaish compared to the over-the-top energy of the rest of the proceedings. It also, for some insane reason, doesn’t feature Bolton, whose energy drives the entire show. The same can be said about Maya Rudolph’s song about key changes, which has the plucky spirit of a Crazy Ex-Girlfriend parodic dissection – this time focusing on a love song’s tendency to kick it into romantic overdrive with a single switch of tonal center – gasps for air by its end.

The special is best when it sticks with the intense Lonely Island tone to leverage Bolton’s calm, understated strangeness. Bolton’s soft sensitivity may have driven him up the adult contemporary charts, but it also absorbs the mania emanating from his surrounding performers and recycles it as charm. When it’s all finally too much for him, he’s also got some delightfully frustrated line delivery (“What the fuck is goin’ on?”).

An Adult Swimmy cake scene and an Eric Andre “Cupid Shuffle” parody aren’t unfunny, they’re just transparent nods to the audience that yes, they did just have Michael Bolton booked for a few days so that any of The Lonely Island or Comedy Bang Bang’s comedian pals that answered their phone could come do their schtick with him. Certainly a special so obviously keyed into Bolton’s viral rebirth as an absurd comic force knows what they have on their hands, but its connective tissue sometimes stretches a bit too thin.

Ending with a Christmas assassination even the aria sung during Mission Impossible: Rogue Nation couldn’t predict is a very Comedy Bang Bang move. Mixing cinematic technique and intentional staginess, marrying the forms into a surreal delight, is the height of mastermind Scott Aukerman’s sensibilities. Of course he’d play it up in this bizarre climax rife with pop culture references and stupidity.

No not Cupidity, though, despite it all, Bolton’s tunes still manage to set the mood. The special even includes some gratuitous sketches for making out so you don’t miss any of the actually funny parts. Breezy and uneven, the special is still worth a watch (even alone) for anyone interested to see how Comedy Bang Bang and The Lonely Island’s humor transitions from their production home bases onto Netflix.

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Jacob Oller writes everywhere (Vanity Fair, The Guardian, Playboy, FSR, Paste, etc.) about everything that matters (film, TV, video games, memes, life).