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Season: 45

Episode date: Nov. 16, 2019

“Ultimately, I’m a very serious musician,” Harry Styles says at the beginning of his monologue before sauntering over to a piano waiting nearby. “And nothing says serious musician like talking and playing piano.”

Then, while “playing” a jazzy interlude on the keys, the pop star riffs about his One Direction bandmates and shares SNL “secrets” before hilariously challenging the audience, “You may be asking yourself, ‘Is he really playing that piano right now?’” Based on B-camera cuts and the fact that the “As It Was” singer then reaches over the piano with both hands to sip a martini as the music magically keeps playing, the answer that is probably no — but you be the judge.

Season: 42

Episode date: Oct. 8, 2016

Lin-Manuel Miranda gives his Hamilton banger “My Shot” a Saturday Night Live remix in his opening monologue, starting out solo on stage before leading a parade of backup dancers into the audience and backstage as he raps about the 2016 presidential election — which at that point was exactly one month away. “The way these grandstanding candidates be talking/ They’re just a tweet away from facing off in Weehawken,” he spits. “They keep brawling, D&RNC keep falling/ I like it better when it’s Kat McKinnon v. Baldwin.”

The highlight comes when Lorne Michaels makes a rare on-camera appearance to request Hamilton tickets and the playwright shrugs the SNL creator off.

Season: 43

Episode date: Nov. 18, 2017

After announcing a $1 million donation to Chicago public schools, Chance the Rapper gives Thanksgiving its long-overdue theme song with the help of the SNL cast — and it’s actually incredibly catchy. As the musician pays tribute to how the holiday is the time many of us are forced into close proximity with awkward relatives, individual cast members dressed as different family member archetypes come in and out. “It’s Thanksgiving time! So say goodbye to all the rules/ Your uncle brought his oxygen, and he’s chain-smoking Kools!” Chance sings while Kenan Thompson rolls by in a mobility scooter, a cigarette hanging out of his mouth.

And for the grand finale, everyone joins Chance on stage to give the ode a wholesome finish: “It’s stuffing and loving and cousins and ovens and belt-notch adjusting — it’s Thanksgiving time!”

Season: 36

Episode date: May 5, 2011

For the last time: he’s not going to sing tonight. For his fourth time hosting, Justin Timberlake vows not to perform, telling the crowd, “In the past when I’ve hosted this show, I’ve also been the musical guest. But tonight is different, okay? Tonight, Lady Gaga is here.”

Then, to show that he means business, the “SexyBack” singer dives into a full musical number dedicated to how he really, really isn’t going to sing — or dance, serenade a lady in the audience or do tricks for cheap applause, for that matter — demonstrating all of the above so that we get the picture.

Season: 39

Episode date: Jan. 18, 2014

While opening his episode of the show, Drake opened up about growing up half Jewish and half Black, telling the audience: “Needless to say, having a Jewish mother and a Black father made for a very interesting bar mitzvah experience.”

With the SNL cast playing members of his family, Drizzy — now fully immersed in a flashback to his 13th birthday — launches into a hilarious rap about his blended cultural background over a beat sampling “Hava Nagila.” “Please don’t forget I’m Black/ Please don’t forget I’m Jewish,” he spits. “I play ball like LeBron and I know what a W-2 is.”

Season: 38

Episode date: Oct. 20, 2012

At the beginning of his monologue, Bruno Mars confesses he’s a “little nervous” — not that you’d ever know it from the show-stopping musical number he then launches into after getting some moral support from Kenan Thompson. “I’ll be amazing, I’ll be great!” he belts, joined by a quartet of background singers for a funky breakdown.

Season: 43

Episode date: May 5, 2018

He really can do anything. During his monologue, Donald Glover — still salty about his past failed auditions for the SNL cast — sings about his endless list of skills while taking a lap through the set, demonstrating what he can (or can’t) do on a skateboard and with lighting equipment. It all leads up to an explosive clarinet solo at the end. You’ve been warned.

Season: 41

Episode date: March 12, 2016

Ariana Grande has done more than one musical monologue on SNL, performing a spectacular tongue-in-cheek Broadway-diva ballad about not wanting to her vocal abilities to hog the spotlight during her second time hosting in 2024. But her 2016 opener takes the cake as her most iconic monologue, with the star poking fun at her own donut-licking slip-up with a hilarious song dubbed “What Will My Scandal Be?”

“A lot of kid stars end up doing drugs or in jail or pregnant, or get caught licking a donut they didn’t pay for … I’ve learned that it’s really time to grow up,” she tells the crowd before fantasizing about her desired “real adult scandal” in a jazzy musical number complete with backup dancers and hilarious interjections from Heidi Gardner and Pete Davidson.

Season: 35

Episode date: Nov. 7, 2009

At 19 years old, Taylor Swift showed up to 30 Rock fully prepared with her monologue song 100% self-written, a rarity for guest hosts. Taking the stage armed with her guitar, the singer expertly makes fun of her own breakup from Joe Jonas, her passion for “writing songs about douchebags who cheat” on her and Kanye West crashing her VMAs acceptance speech two months prior.

Hilariously embodying a doe-eyed caricature of herself, the singer gets audience members giggling from her opening lines: “I like glitter and sparkly dresses, but I’m not going to talk about that in my monologue/ I like baking and things that smell like winter, but I’m not going to talk about that in my monologue.”

Episode: Season 2, episode 8

Paul Simon hilariously tries — and quickly regrets — breaking down his “Mr. Alienation” image by performing “Still Crazy After All These Years” in an extravagant turkey costume, well-timed for SNL‘s pre-Thanksgiving episode in 1976. After a few bars, the iconic singer-songwriter cuts the music and hilariously deadpans, “You know I said when the turkey concept was first brought up, I said, ‘There’s a very good chance I’m gonna end up looking stupid.’”

“I felt it was not in any way keeping in my image,” he continues as audience members howl with laughter. “They said, ‘Hey, you know, you take yourself so seriously. Loosen up a little bit.’”

Calling the ordeal a big “mistake,” Simon then steps off stage to change — but not before airing out his grievances to Lorne Michaels.