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Examining the timeless, enduring appeal of “The Way You Look Tonight”

In Hear ThisA.V. Club writers sing the praises of songs they know well—some inspired by a weekly theme and some not, but always songs worth hearing. This week, in anticipation of the Oscars, we’re going through some of our favorite Best Original Song winners.

Swing Time is probably my least favorite Fred Astaire and Ginger Rogers movie, but it’s redeemed by one of my favorite tunes—the Best Original Song Oscar-winner, “The Way You Look Tonight.” In the 1936 film, Astaire plays Lucky, a part-time dancer and full-time hustler who gambles his way into making a living. The opening setup is that Lucky misses his own wedding—because he got delayed betting on the likelihood of his upcoming nuptials—and has to go to New York to earn $25,000 and prove his worth to his erstwhile fiancée. Trapped in a conceit that could only happen in this type of movie, Lucky and Rogers’ Penny embark on a series of misadventures that force them to dance their way into love. Penny’s arctic-cool demeanor finally begins to warm when Astaire sings this song, marking a clear turning point in their previously bumpy relationship.

This composition won the award in only the third year of the category’s existence, yet has gone on to become a standard, and one of the most covered songs to have taken the prize. So what’s made this 80-year-old tune endure? Perhaps it’s that Jerome Kerns’ melody fits so effortlessly into Astaire’s admittedly limited vocal range and that Dorothy Fields lyrical depiction of the first blush of love is timeless. The song is repeated throughout the film, popping up in several situations, and by the time the closing credits roll any first-time viewer will recognize it. It has long been a go-to selection for singers. Bing Crosby, Billie Holiday, Doris Day, and Ella Fitzgerald chose it. Frank Sinatra’s 1964 version has become the often-imitated benchmark. Artists who plunder the classic American songbook for their signature style of über retro cool (Harry Connick, Rod Stewart, Michael Bublé) consistently choose it. Hell, Wonder Woman and Dexys Midnight Runners gave it a go, for goodness’ sake. It even manages to hit that pseudo-nostalgic sweet spot of our current age (Sara Bareilles, Maroon 5), as evidenced by Seth MacFarlane’s performance during Charlize Theron and Channing Tatum’s incredibly awkward ballroom dance at last year’s Oscar ceremony.

With so many choices, it’s hard to pick a favorite version. Fitzgerald’s version awards it the lush orchestral treatment her sonorous pipes demand. But for my pick, I just might go with The Jaguars’ 1956 doo-wop version. It’s such a charming blend of trends from two long-ago pop-music eras. Then again Mouse Rat‘s rockabilly-leaning version from a season-two episode of Parks And Recreation, is utterly winning its very specific Andy Dwyer way.

“The Way You Look Tonight” is one of those special songs that’s old-fashioned in a way that implies classic, not staid. It evokes a bygone era where even a fast-talking hustler like Lucky needed a bottomless supply of tops, tails, and spats to get shit done—at least the fast-talking hustlers who danced their way into the night’s winnings did.

Note: Swing Time has taken a place a bit lower in my estimation due to Astaire’s blackface ode to Bill Robinson and John W. Bubbles, “Bojangles Of Harlem.” As an adult capable of discerning nuance, I see that this number is a more reverential account of the little-appreciated art form of tap dancing and is distinct from the Al Jolson variety. But as a kid first watching these films on Turner Classic Movies on a lazy weekend afternoon with my mom, I just knew “blackface equals NOPE.”