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Shortly before writing the song that would become his first single in six years, Justin Timberlake worked with his musical director Adam Blackstone on an arrangement of John Lennon’s “Jealous Guy,” in the style of Donny Hathaway’s famous cover.

As they rehearsed the version that Timberlake would sing at a small jazz club where Blackstone had a residency, they discussed the song and, as Timberlake recounted in a recent interview with Zane Lowe, “the idea that you just don’t hear that from men often — that they would express an emotion that makes them vulnerable.” Inspired by Lennon and Hathaway’s soul-baring, the lyrics to “Selfish,” the lead single from Timberlake’s new album, “Everything I Thought It Was,” began to pour out.

A truly vulnerable Justin Timberlake — one stripped of the Teflon charm that has coated his music and career thus far — is a tantalizing concept, especially at this moment. In the years since his minor 2018 misstep “Man of the Woods,” Timberlake’s image has tarnished somewhat. Audiences are reconsidering mid-2000s pop cultural events like the Janet Jackson wardrobe malfunction seen ’round the world at the Super Bowl halftime in 2004, and the media’s cruel treatment of Britney Spears, Timberlake’s ex-girlfriend.

In February 2021, amid the re-evaluation of Spears’s career and nearing the end of her court-ordered conservatorship, Timberlake posted a long, since-deleted statement on Instagram, apologizing specifically to Jackson and Spears. He added, “I am deeply sorry for the times in my life where my actions contributed to the problem, where I spoke out of turn or did not speak up for what is right.”

Is “Selfish” a musical reckoning with all of this? Well, not exactly. The song does bear some sonic hallmarks of introspection: It’s muted, minor-keyed and sung in a slightly deflated tone. But, lyrically, Timberlake seems to have confused vulnerability with humblebragging. “It’s bad for my mental,” he sings in his nimble croon. “But I can’t fight it when you’re out lookin’ like you do, but you can’t hide it.” This is not exactly a soundtrack for dismantling masculine bravado: The song’s most intimate confession is that Timberlake gets jealous when other men look at his girl — and that they are always looking at his girl, because damn, she is hot.

Still, the song debuted at the respectable, if not spectacular, position of No. 19 on the Billboard Hot 100, and, after he performed it on the Jan. 27 episode of “Saturday Night Live,” it was warmly received by one unexpected well-wisher. “I am in love with Justin Timberlake’s new song ‘Selfish,’” Spears wrote on Instagram the next day, in a post where she also apologized “for some of the things I wrote about in my book.”