Just In: Sabrina Carpenter Is Vying for Grammy Nods in Top Categories With 2 Different Hits — Hey, It Worked for These Acts…. See More

Artists generally pick their strongest hit from the year and enter it in the Grammy competition for both record and song of the year. That’s what such artists as Billie Eilish (“Birds of a Feather”), Beyoncé (“Texas Hold ’Em”) and Ariana Grande (“We Can’t Be Friends (Wait for Your Love)”) did this year. This Grammy strategy can be summarized in the immortal words of Pat Benatar: “Hit Me With Your Best Shot.”

But sometimes, artists enter different hits for record and song of the year. Sabrina Carpenter is taking that approach this year. “Espresso” is vying for a nod for record of the year. “Please Please Please” is competing for a nod for song of the year.

Carpenter and Amy Allen were among the co-writers of both songs. They co-wrote “Please Please Please” with Grammy darling Jack Antonoff. They co-wrote “Espresso” with Steph Jones and Julian Bunetta. This entry strategy may be good news for Antonoff, who is also competing for a song of the year nod for “Fortnight,” which he co-wrote with Taylor Swift and Post Malone. But it was bad news for Jones and Bunetta, perhaps costing them a song of the year nomination. (There is no best pop song category, so we can say with certainty that “Espresso” will not be up for a songwriting Grammy.)

Allen and Jones are both vying for nods for songwriter of the year, non-classical. Allen was nominated in the category two years ago, which was the category’s inaugural year.

Carpenter’s camp also submitted “Espresso” (rather than “Please Please Please”) in the best pop solo performance category.

Let’s scroll back through all the times an artist was nominated for record and song of the year with different hits. We’re including all songs that were at least co-written by the artist (or a member of the group, in the case of groups). But we’re not including songs that the artist didn’t write or co-write, because the song of the year nomination didn’t go to them. The years shown are the years of the Grammy ceremony.

Notes: The Beatles’ earth-rattling breakthrough smash “I Want to Hold Your Hand” was nominated for record of the year, but the song of the year nod went to the title song from their first film. John Lennon and Paul McCartney co-wrote both songs, both of which had multiple weeks at No. 1 on the Billboard Hot 100. This was the only Grammy nomination for “Hand.” “A Hard Day’s Night” was also nominated for best performance by a vocal group and best rock & roll recording. It won the vocal group award.

“A Hard Day’s Night” was the first rock song to receive a Grammy song of the year nod. The song failed to receive an Oscar nod for best original song. That was the Oscars’ loss – can you imagine the Fab Four taking the stage on April 5, 1965 at the Santa Monica Civic Auditorium, which hosted the Oscars in those days? Even if they’d lost to that year’s winner, “Chim, Chim Cher-ee” from Mary Poppins, they would likely have stolen the show. (No shade to The New Christy Minstrels, who performed “Chim” on the telecast.)

Notes: “It’s Too Late” was the lead single from King’s era-defining album Tapestry, which also featured “You’ve Got a Friend.” King graciously let James Taylor release his version of the latter song as a single. His soothing rendition very nearly followed “It’s Too Late” into the No. 1 spot on the Hot 100. (The Raiders’ “Indian Reservation (The Lament of the Cherokee Reservation Indian)” snuck in for one week in the top spot in between the two King-written hits.) Taylor’s version was also nominated for record of the year and won for best pop vocal performance, male.

These were Lauper’s first two Hot 100 hits. “Girls” peaked at No. 2 (it couldn’t get past Van Halen’s “Jump”). “Time After Time” reached No. 1. This was the only nod for “Time After Time,” which Lauper co-wrote with Rob Hyman, best-known as a founding member of The Hooters. “Girls” was also nominated for best pop vocal performance, female. Lauper performed “Time After Time” on the Grammy telecast in 1985.

Jazz legend Miles Davis recorded an instrumental version of “Time After Time” in 1985. “The most honored I ever felt was when Miles Davis covered it,” Lauper once stated

Both of these hits were entered for (that is to say, vied for nominations for) both record and song of the year. The voters simply picked different hits in these two categories. Both hits had multi-week stays at No. 1 on the Hot 100. “No Scrubs” won a Grammy for best R&B performance by a duo or group with vocal. “Unpretty” was nominated in two other categories – best pop performance by a duo or group with vocal and best short form music video. Group member Tionne “T-Boz” Watkins co-wrote “Unpretty” with producer Dallas Austin. TLC performed a coupling of the two hits on the Grammy telecast in 2000.

Both of these hits were entered for both record and song of the year (as was a third U2 hit, “Elevation”). The simply voters picked different hits in these two categories. “Stuck” won best pop performance by a duo or group with vocals. “Walk On” was also nominated for best rock song. “Walk On” wasn’t much of a hit single – it bubbled under the Hot 100 at No. 118. “Stuck” did better, reaching No. 52 and remaining on the chart for 20 weeks. U2 opened the 2002 Grammy telecast with a performance of “Walk On,” which gained extra resonance in the wake of the 9/11 terrorist attacks the previous September

In a truly head-scratching move, “Single Ladies” wasn’t entered for record of the year. “Halo” and “If I Were a Boy” were. Those were both big hits – both made the top five on the Hot 100 – but they were not as big as “Single Ladies,” which logged four weeks at No. 1 and was propelled by an iconic video (“one of the best videos of all time,” in the memorable words of one pop-culture authority.)

If “Single Ladies” had been entered for record of the year, would it have been able to beat that year’s winner, Kings of Leon’s “Use Somebody”? We’ll never know for sure, but it certainly seems possible. Beyoncé co-wrote “Single Ladies” with Christopher “Tricky” Stewart, Terius “The-Dream” Nash and Thaddis Harrell. “Single Ladies” also won best R&B song and best female R&B vocal performance. “Halo” won best female pop vocal performance.

The Story of O.J.” was Jay-Z’s only entry for record of the year. “4:44,” which Jay co-wrote with Dion (“No ID”) Wilson and Kanan Keeney, was his only entry for song of the year. Both hits received additional nominations. “O.J.” was also nominated for best rap song and best music video. “4:44” was also nominated for best rap performance. Both songs cracked the top 40 on the Hot 100. “O.J.” reached No. 23; “4:44” hit No. 35.

This was the year Jay-Z went 0-8 at the Grammys. He made his displeasure known in his song “Apeshit”: “Tell the Grammys f–k that 0-for-eight shit.” “Apeshit” was featured on The Carters’ Everything Is Love, which won a Grammy (phew) for best urban contemporary album the following year.