Jerome Kern and Dorothy Fields composed the ballad, "The Way You Look Tonight" in 1936 for use in the film Swing Time (RKO Radio Pictures). The song won the Academy Award for Best Original Song that year. The song has since gone on to be recorded by many notable vocalists. We will consider five of these here.
Fred Astaire, Brunswick 7717, 1936
If sound had color, this performance would be a beautiful sepia. Famous for his dancing, Fred Astaire was also a very fine singer, who lived in the shadow of his friend, Bing Crosby. Astaire's movie version of this song was recorded on July 24. The performance is limited (or liberated) by the technology of the day. Astaire's voice is flat, lacking any of the artificial enhancements available today. It is imaged well in front of the accompaniment. Sweet and simple, Astaire's character, John "Lucky" Garnett, sings to his dance partner, Penny, played by Ginger Rogers, through her bedroom door while she is getting ready to perform. Pure magic.
Billie Holiday, Brunswick 7762, 1936
Before the ink could dry on the record labels of Astaire's performance, pianist Teddy Wilson brought a 21-year-old Billie Holiday into the studio to record the song with a small ensemble that included pianist Teddy Wilson, trumpeter Irving 'Mouse' Randolph, clarinetist Vido Musso, saxophonist Ben Webster, guitarist Allan Reuss, bassist Milt Hinton, and drummer Gene Krupa. On this swing-era performance, Holiday does not enter until about 1:27 after Musso, Randolph, and Wilson have all riffed. These are the singer's salad days and she stretches time in her phrasing and delivery, almost stepping out of the counted time altogether. This is light years beyond Astaire and recorded only 10 weeks after his studio date.
Frank Sinatra - Days of Wine And Roses, Moon River, And Other Academy Award Winners (Reprise Records, 1964)
The man strides confident and determined toward the studio doors wearing a natty tweed coat over slacks, white shirt, and dark tie, his trademark Triby is slanted rakishly over one eye. Smelling of lavender and cigarettes with a mere hint of Jack Daniels, he stubs out his smoke in the sand-filled ashtray beside the double doors he pushes through, pulling loose his tie, and acknowledging the musicians and director, Nelson Riddle. The downbeat given, the man continues to the microphone and music stand while the music plays, where, stepping up, on queue, he confidently expels, "Some...day..."
Tony Bennett - My Best Friend's Wedding Soundtrack (Madacy Records, 2007)
The antithesis of the Chairman's performance: Tony Bennett recorded "The Way You Look Tonight" several times, first, on his LP Long Ago And Far Away (Columbia, 1958) and his Duets II (with Faith Hill, Columbia, 2011) and Viva Duets (with Thalia, Columbia, 2012). But it was his interim recording made with pianist Ralph Sharon that struck close to perfect. Where Sinatra sings the song as if he were Lord Byron throwing off a verse here and there, Bennett slows things down, simplifying them to provide us the essence of the lyrics as if they were some essential cognac heated in an ancient snifter.
Cassandra Wilson - Coming Forth By Day (Legacy, 2015)
By the time Cassandra Wilson had recorded this last recording (to date) as a leader, she had redefined jazz vocals completely. Coming Forth By Day was her tribute to Billie Holiday on the centenary of the singer's birth. Wilson combines the inventive orchestration of her past recordings with strings to present one of her most straightforward treatments of vernacular jazz. Her deep alto voice and slow tempo come close to equaling that of Tony Bennett. By any estimation, this performance of the ballad is sumptuous and lush, with Wilson's voice buried deep in mystique and technique.