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According to Mueller: "Constructed sparsely in a kind of theme and variations form (ABA'A") it is particularly notable for the appealing way the strains link up – especially for the poised and dramatic transitions between the A' and A" strains".
Mercer recalled working with the older Kern, and how Kern reacted to the lyrics for "I'm Old Fashioned": "We hit it off right away. I was in such awe of him, I think he must have sensed that. He was very kind to me, treated me more like a son than a collaborator. And when he thought I had a great lyric he said, 'Eva, Eva, come down here', and he kissed me on the cheek and he said, 'Eva, I want you to hear this lyric'. Well, of course I was thrilled that he liked it that much, you know. 'I'm Old Fashioned', that one was."
The first recording was made in 1942 by Astaire with John Scott Trotter and his orchestra (Decca 18490). It was then sung by Judy Garland, Dinah Shore, Julie Andrews, Andy Williams, Blossom Dearie, The King Sisters, and since the 1980s by artists like Cassandra Wilson, Maria João (both as up-tempo tunes), Stacey Kent and Victoria Williams. It was also part of the early crossover attempt by classical soprano Eileen Farrell in 1960 with her album I've Got a Right to Sing the Blues. Jessye Norman followed her example in 1984 (With a Song in My Heart).
Beside the vocalists "I'm Old Fashioned" has been recorded by John Coltrane as a sensitive hard bop ballad in 1957 for his album Blue Train, featuring trombonist Curtis Fuller, Lee Morgan on trumpet and Kenny Drew on piano. Trumpeter and singer Chet Baker recorded the song several times, at first in 1958 on the album (Chet Baker Sings) It Could Happen to You.
Nevertheless the song has been predominantly interpreted by pianists like George Shearing, Oscar Peterson, Dave Brubeck, Jimmy Rowles, Al Haig, Ahmad Jamal, Phineas Newborn Jr., Hank Jones, Tommy Flanagan, Kenny Drew, Marian McPartland, Cedar Walton, Sadao Watanabe, McCoy Tyner and Joanne Brackeen.