‘Saturday Night Live’ has a rich, half-century musical history. Questlove’s new documentary digs in

The startling “cold open” for a documentary about 50 years of “Saturday Night Live” music is proof that a musician — a specific kind of musician — had to put it together.

It’s a mashup of performances from artists that few people would think of putting together, like R.E.M. and Morris Day, Rick James and Duran Duran, Hanson and Cher. Filmmaker Ahmir “Questlove” Thompson’s experience as a DJ taught him enough about beats per minute and musical keys to meld things seamlessly.

The thrill ride took 11 months to put together and stretched to 17 minutes, until the need to edit took it down to around five minutes.

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“I thought, what am I going to add to the table that’s different from anybody else?” Questlove said in an interview. “My music gave me a third language that maybe other documentarians don’t have. I’ve got to stretch that muscle.”

The special, “Ladies and Gentlemen … 50 Years of SNL Music,” is given the entirety of NBC’s prime-time Monday night and begins streaming the next day on Peacock. There’s so much material that fans will inevitably yearn for things that were left out.

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Questlove was put on the project by “Saturday Night Live” executive producer Lorne Michaels shortly after the 2021 release of “Summer of Soul (…or, When the Revolution Could Not be Televised)” revealed Thompson’s heretofore unknown skill as a filmmaker.

He first thought of something simple, like the 50 best performances in 50 years, but discarded that idea. “I didn’t want it to be ‘the world according to Questlove — here are the best performances,’ and then I miss one.,” he said.

The show recalls many memorable performances, with artists discussing how meaningful it is to be invited. “It changes the way that you’re seen in a way that no other show can do,” Miley Cyrus says.

There are plenty of entertaining anecdotes. Tune in to find out why Rage Against the Machine made the U.S. Secret Service nervous. Controversies are dissected — Sinead O’Connor tearing the pope’s picture, Kanye West’s MAGA meltdown — and put in perspective: there was more “show biz” involved in Elvis Costello’s abrupt song switch than was apparent at the time.

Yet the film’s richness comes in reminding viewers how richly music has been integrated into “Saturday Night Live’s” comedy through the years, with musical guests added to skits and short films like “Lazy Sunday.” In one priceless skit, Fred Armisen plays the dad at a wedding who rips the room apart by reuniting with his old punk band, including a wigged Dave Grohl on drums.

“Music is driving the show in a way that was both obvious and not obvious at the same time,” said Oz Rodriguez, who produced the special with Questlove.

One thing that struck Questlove: how many memorable moments began with doubt. Eddie Murphy initially rejected the idea where he was to impersonate James Brown singing at a hot tub party. Joe Piscopo was worried about how Frank Sinatra would react to him “playing” Sinatra in an “Ebony and Ivory” duet.

And Jimmy Fallon was afraid to talk to Mick Jagger about a skit where he played Jagger talking to the real thing in a “mirror,” key to Fallon’s career trajectory. “Jimmy stepping into his destiny means me talking to you at this moment,” said Questlove, whose band the Roots became house band on the “Tonight” show when Fallon took over that franchise.

‘SNL’ was a big part of Questlove’s path

Questlove, 54, credits “Saturday Night Live” for a big part of his musical education.

Growing up in Philadelphia, he was permitted by his parents only to watch music or educational shows on television. They often would wake him up to watch “Soul Train,” which aired at 1 a.m. in his market, or earlier so he could catch musical performances on “SNL.”

The show had an eclectic mix of musical guests in its early years, something the documentary pays tribute to by interviewing the late “SNL” music producer Hal Willner. It shows a portion of a Captain Beefheart appearance that so flummoxed the audience that it reacted with complete silence when he was done.

“Watching ‘SNL’ those first seasons gave me a musical vocabulary that I don’t think would have happened on its own,” he said.

Preparing the documentary, Questlove downloaded 50 years’ worth of episodes onto his computer and playing them constantly at his home — even overnight with the sound turned down. If something caught his eye, he took notes.

The exhaustive approach led to a world of discoveries, or rediscoveries. In one memorable segment, the film goes backward in time through performances by rap artists, from Kendrick Lamar to the first one, Funky 4+1, introduced by Blondie’s Deborah Harry in 1981.

Among the key musical moments the producers talk about in interviews are Steve Martin’s “King Tut” song, the legendary “more cowbell” skit and a ferocious performance of “Rockin’ in the Free World” by Neil Young.

None of them, however, is included in the film. The first two skits are covered extensively in other documentaries, so they didn’t want to be repetitive. As for Young, they only had so much time. “I could actually do maybe three sequels,” Questlove said.

Questlove has had his own extensive history with the show, appearing in skits, onstage with the Roots playing backup to Busta Rhymes and Toots and the Maytals, to sitting in the audience as a fan. One exception: He’s never been the musical guest. But he noted that the Roots have an album coming later this year.

“I still have dreams,” he said.