▶ Listen on Spotify, Apple Music or YouTube
3. Ariana Grande: “R.E.M.”
Singer Grande, to fans; three letters. Thanks to the commonly used collections of letters that make up both her first name and her nickname (“Ari”), the first-time Oscar nominee Ariana Grande is one of contemporary pop music’s most ubiquitous names on the crossword grid. And in the highly unlikely event that you ever encounter the very specific clue “fourth track on Ariana Grande’s rather underrated 2018 album ‘Sweetener,’” this song provides that three-letter answer, too.
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4. Etta James: “All I Could Do Was Cry”
Blues singer James; four letters. Since Etta James’s last name is also a popular first name, that clue can cause some confusion for the uninitiated — but experienced crossword-ers know the answer. Though she’s sometimes also conjured by a mention of her most famous song, “At Last,” my favorite track on James’s debut album of the same title is this wrenching, scorchingly sung ballad of lost love.
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5. Arlo Guthrie: “The City of New Orleans”
Folk singer Guthrie; four letters. This classic crossword clue has tripped up many a newbie, confidently scrawling “Woody” onto a puzzle before realizing there’s no room for the “y.” The answer is Woody’s son, who has an especially grid-friendly first name: Arlo. And while Arlo is best known for a certain 18-minute, Thanksgiving-associated talking blues, nothing derails the flow of a playlist like sticking “Alice’s Restaurant Massacree” right in the middle. (You are free to listen to it on your own time, if you must.) Instead, here’s the biggest chart hit of Guthrie’s career, a 1972 cover of Steve Goodman’s rousing ode to American train travel.
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6. Yoko Ono: “Death of Samantha”
“Double Fantasy” singer; three letters. Well, if “Lennon” doesn’t fit, it’s got to be “Ono.” Let’s honor the great conceptual artist/musician with a track from one of her best solo albums, the 1973 release “Approximately Infinite Universe.” “People say I’m cool,” Ono croons, although as this song unfolds, the devastating tumult beneath that reserved exterior begins to show.
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7. Sia: “Cheap Thrills”
Singer with the 2016 No. 1 hit “Cheap Thrills;” three letters. That was an actual clue from a Times puzzle earlier this week, and the answer — which my boyfriend did not know — was Sia. He probably wishes I sent this playlist out a little sooner.
▶ Listen on Spotify, Apple Music or YouTube
8. Adele: “When We Were Young”
Singer with albums “19,” “21,” “25” and “30;” five letters. Those bookend vowels, her household-name status, the satisfying succinctness of a mononym — Adele is a crossword creator’s dream! Not to be one of those people who brags about having seen Adele’s Las Vegas residency, but — when I saw Adele’s Las Vegas residency, her emotional performance of this 2015 ballad got me all weepy.
