Legend has been in the repertory-hits class of celebrity singers for some time—the Christmas album variety—but he has plenty of his own songs, too. Several, including “Ordinary People,” came from his debut album, Get Lifted, of which he’s touring to celebrate the 20th anniversary. 

Moctar’s shredding, psychedelic guitar songs—he plays in the distinct Tuareg genre and sings in the Tamasheq language—first reached a global audience via a compilation album from Portland record label Sahel Sounds; Music from Saharan Cellphones compiled MP3 tracks that were, until that point, exchanged hand-to-hand throughout the Sahara. He’s since released a handful of albums with Matador, including Funeral for Justice, in 2024, and an acoustic version of that album titled Tears of Injustice this winter. 

Like most from the Odd Future collective—which once included Syd, Frank Ocean, Tyler, The Creator, and many others—Earl Sweatshirt has forged an identity entirely his own in the group’s aftermath. Far from pop stardom, he’s maintained a high profile without budging from what The New York Times recently described as “lo-fi, subterranean, lyrically abstruse rap music.” Live Laugh Love, his latest, came out in August. 

Pink Martini on New Year’s at the Schnitz—what else is there to say? The hometown hero, jazzy big-little pop orchestra knows how to ring in a new year; famously, they did it for years with the LA Philharmonic at the Walt Disney Concert Hall. 

Hey John Legend, Typhoon is 20, too! In the show notes for this pair of anniversary dates, the famously big band recalls playing “murder ballads and Gregorian chants and sea shanties” at the Clinton Street Theater as teens in 2005. House shows, a record with Portland’s Tender Loving Empire, and they were on Letterman by 2011. Black Belt Eagle Scout opens the Friday show and Lost Lander opens Saturday. 

Cate Le Bon’s songs are so beautifully structured. Listening to her jangly, dark-twinged pop feels like being in the hands of a great author. It’s no surprise, then, that the Welsh singer is also a record producer who’s worked with the likes of Wilco, Devendra Banhart, Kurt Vile, and Horsegirl. Michelangelo Dying came out this fall. 

Under the moniker Sudan Archives, Brittney Parks makes what she calls orchestral Black dance music. In other words, she’s a pop star who sways between rapping and R&B hooks. Her violin leads everything, but the “orchestra” comes from an eclectic mix of beats and synths and, on her third full-length album, The BPB, an increasing interest in sounds modified and playing off of what she calls “gadgets.” 

Plenty of people are famous for being famous in 2025, but few have mastered the art like Cardi B; fewer still have managed to immortalize so much discourse in their actual art. She was a social media and then reality TV star before her 2018 debut, Invasion of Privacy, which won her a Grammy for best rap album—the first woman ever to win the award. Despite taking seven years to produce, her second album, titled Am I the Drama?, only continued her dominating path. 

Charlyn Marie “Chan” Marshall, a.k.a. Cat Power, has been your favorite singer’s favorite singer for more than 20 years, but her landmark record, aptly titled The Greatest, turns 20 in the new year. Coordinated with the anniversary tour, of the “playing the whole album plus some other tracks” variety, Marshall is releasing the EP Redux, with covers of James Brown’s “Try Me” and Prince’s “Nothing Compares 2 U,” as well as a new version of “Could We,” from Greatest.