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Frank Sinatra’s Playful Side: The Story Behind “Ol’ Macdonald”

Andy Frye

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Even legends need to have fun sometimes; Frank Sinatra’s playful recording of “Ol’ Macdonald” reveals a rarely seen side of the Chairman of the Board; one that wasn’t afraid to be silly. This unexpected farmyard romp, arranged by the great Nelson Riddle, shows how Sinatra could turn even a children’s song into a swinging jazz number with his signature style.

In a fascinating 2019 interview, legendary lyricist Alan Bergman shared behind-the-scenes stories about Sinatra’s recording session for this novelty track. Bergman recalls how Sinatra’s perfect comic timing and Riddle’s clever arrangement transformed the simple nursery rhyme into something special; proving no song was beneath the master’s touch when approached with creativity.

Alan Bergman on Frank Sinatra’s ‘Ol’ Macdonald’

Fans remain divided about this quirky recording; some adore its lighthearted charm while others consider it an oddity in Sinatra’s catalog; but most agree it showcases his versatility. As one commenter noted, “Only Frank could make ‘E-I-E-I-O’ sound cool.” The track remains a fun reminder that even serious artists shouldn’t take themselves too seriously.

The 1999 remastered version brings new life to this novelty recording, with crisp audio that highlights Riddle’s playful orchestration. Hearing Sinatra deliver animal sounds with perfect pitch and swing reminds us that musical genius can shine even in the most unexpected places.

Ol’ Macdonald (1999 Remastered)

What makes this recording special isn’t the song itself, but how Sinatra elevates it. His impeccable phrasing turns simple lyrics into musical gold, while Riddle’s arrangement adds sophisticated jazz touches. Together, they prove that great artists can find creative potential anywhere; even in children’s singalongs about farm animals.

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For those wanting to explore more of Sinatra’s playful side, his official YouTube channel offers treasures from throughout his career. While “Ol’ Macdonald” may not be his most serious work, it’s an important reminder that musical mastery includes knowing when to have fun; something Sinatra understood better than anyone.

Sinatra: Nothing But The Best (Remastered)