A look, if you will:
Jenny and Johnny:

Lady Gaga:
Blair Waldorf somehow finagled Lady Gaga into performing at a retelling of Snow White at NYU to impress the snobby theater kids. What does nonsensical theatrics and Snow White have in common? Who knows, but I bet Gaga would work on something with those dwarfs. Watch here. Oh, and of course Hilary Duff is dating Dan in this episode, which we think maybe counts as another musical guest.
Cyndi Lauper:
Pouty Blair is upset that her mother wants to go to a Cyndi Lauper concert instead of attending her own 18th birthday party. (What 18 year-old wants her mother at her birthday party?) So Cyrus convinces Cyndi to perform at Blair's bash instead, which Blair ditches promptly to win over Chuck, presumably. Here you go, watch it.
Florence and the Machine:
In Gossip Girl's first homage to Fashion's Night Out, Florence and the Machine play at W Magazine's party.
Robyn:
Dan leaks a video of drunk Blair singing “Stand by Your Man,” which is horrifically embarrassing for some reason, and invites Robyn to introduce the video at Blair's birthday party. She sings, too, as you can see here.
Lisa Loeb:
At a sad launch party for Rolling Stone's "Top 10 Forgotten Bands of the '90s," Lisa Loeb stays with Rufus Humphrey, former rock star and, who I might add, is both the father of Dan AND step-father of Dan’s ex-girlfriend who also took his virginity, Serena (oh the lives they lead). Watch it here. Check out those eyeglasses!
No Doubt:
No Doubt played their cover of “Stand and Deliver” in the show’s attempt to launch an 80s spin-off, where the prim young Lily (mother of Serena) navigates the punk-rock scene in California. Thankfully, the series was never picked up. Gwen Stefani, here.
Sonic Youth:
Yup, the king and queen of indie rock appeared on Gossip Girl. Thurston Moore and Kim Gordon had the honors of marrying Lily and Rufus and played an acoustic song, too. They also get credit for appearing on Gilmore Girls (with Yo La Tengo!). Watch Sonic Youth sing sentimentally here; just try to tune out the Italian overdubs.
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