The Artistic History Behind Frank Sinatra’s “The Way You Look Tonight” via Jacob Harris/ASSOCIATED PRESS

Everyone knows ?The Way You Look Tonight.? This classic song is a staple at weddings, in movies, or for any situation where romance is key. The lyrics are adoring and frank; the subject of the song makes everything better. She is so lovely in this moment that the singer is totally free from worry. Her warmth so comforting, her ?breathless charm” so captivating. Backed by a swinging band, each verse bounces confidently like a love poem in itself. Frank Sinatra?s version of the standard, recorded in 1964, reigns supreme in our culture but he was not the first singer to croon out ?The Way You Look Tonight.? And he certainly was not the last.

Swing Time

?The Way You Look Tonight? was first composed by songwriters Dorothy Fields and Jerome Kern for the 1936 musical comedy film Swing Time, starring Ginger Rogers and Fred Astaire. In Swing Time, Astair plays Lucky, the fast-talking dancer with a gambling addiction, in cahoots with Rogers as a frosty dance instructor named Penny. Though it?s not the most beloved Astaire-Rogers collab, the introduction of ?The Way You Look Tonight? along with Astaire and Rogers? famous ?Never Gonna Dance? sequence of make up for a convoluted plot.

Fred Astaire, as Lucky, first performs ?The Way You Look Tonight? while seated at the piano in Penny?s apartment. Ginger Rogers hovers in the bathroom, shampooing her hair over the sink. Astaire begins to tap on the piano casually, easing into the number that would go on to win an Academy Award for Best Original Song. What starts as a lighthearted apology to Penny, unfurls into a foxtrot ballad that fully commands her attention. The camera cuts between Astaire, singing softly over the piano, to Rogers in the bathroom, her head covered in suds. Without actually seeing the woman he?s serenading, ?The Way You Look Tonight? ? in its original form ? lacks the physical connection which seems to drive later versions.

?The Way You Look Tonight? often brings to mind the vision of a beautiful woman, dolled up and ready for the night. But here, as Penny, Ginger Rogers is completely caught off guard during her morning routine. Lucky?s song marks a softening shift in her character, and the beginning of a spark between the two leads. When the tune is later reprised in ?Never Gonna Dance? (watch below), Rogers does fulfill the vision in a gown. And without any words, the pair finally unites over the strong melody ? through dance.


“Never Gonna Dance”

The Long Tradition of ?The Way You Look Tonight?

After the success of Swing Time, specifically its Oscar-winning hit, ?The Way You Look Tonight,? musicians were scrambling to record their own covers of the song. Just ten weeks after Swing Time hit theaters, Billie Holiday released her own jazzy, orchestral version. (Holiday was just 21 years old at the time.) This first example of taking creative liberty with ?The Way You Look Tonight? leans on a full swing band, led by pianist Teddy Wilson.

Following Billie Holiday, Bing Crosby and his wife Dixie Lee recorded ?The Way You Look Tonight? as a duet. In 1942, famed big band leader Benny Goodman gained radio play with his own version of ?The Way You Look Tonight? which featured Peggy Lee on lead vocals. ?The Way You Look Tonight? even became the first hit for The Lettermen in 1961. But three years later, Frank Sinatra would release his own cover and completely redefine the future of this versatile love song.

Frank Sinatra?s Version

In his 1964 album The Days of Wine and Roses, Frank Sinatra focused on recreating the category of Oscar-winning original songs. This includes “Moon River” and more Academy Award-recognized tunes. Among them, ?The Way You Look Tonight,? from Swing Time, which Sinatra sang with the Nelson Riddle Orchestra ? officially creating the version to beat. Most subsequent singers, like Tony Bennett, try to emulate Sinatra?s affable dazzle in their own covers. The accompanying Nelson Riddle Orchestra also set the bar for the instrumental?s neat, sophisticated style. Through the decades, Sinatra?s musical embellishments have been reprinted and retaught as the songbook standard for this oft imitated crowd-pleaser.


Beyond unifying the various spirits of ?The Way You Look Tonight,? the song also became a favorite among the Frank Sinatra canon. It?s revered and played alongside all of Ol’ Blue Eyes? original pieces. Despite lyrics that center wholly on the singer?s awe-inspiring partner, Sinatra manages to exude the same confidence which characterizes his more personal repertoire: ?I?ve Got the World on a String,? ?My Way,? ?The Best is Yet to Come,? “Fly Me to the Moon,” the list goes on. The unique take resonates with audiences to this day.

A Song That Endures

While Frank Sinatra?s interpretation of ?The Way You Look Tonight? may sound dated, it?s come to stand in for the archetypical idea of affectionate, old-fashioned courtship. You don?t need to be a connoisseur of old Hollywood culture to know this catchy tune and understand the nostalgia it inspires. Playing ?The Way You Look Tonight? at an event can seem like a kitschy choice… until the verses unfold into utterly buttery romance. The swinging pull of the orchestra is both undeniable and sweetly familiar. And of course, Sinatra?s cheeky charm kicks everything up a notch. “The Way You Look Tonight? is not cliché. It?s classic, like a sparkling glass of champagne. Or Ginger Rogers and Fred Astaire.

So, it?s no surprise that ?The Way You Look Tonight? has become one of the most in-demand wedding songs. Watch below for some fun examples of this tradition in cinema.


My Best Friend?s Wedding

Father of the Bride

Watch: You Can Rent Frank Sinatra?s Beautiful Palm Springs Home

Emily Mack About the author:
Emily Mack is a staff writer for Rare. She currently lives in Chicago and has very strong opinions about where to find the best hot dog. She studied nonfiction writing at Columbia University in New York City, and recently graduated with the Ellis Avery Prize for creative writing. Her favorite topics are Cher, fast fashion, Chicago urban legends, and Jack Nicholson movies.
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