When You’re Smiling

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“When You’re Smiling (The Whole World Smiles With You)” arrived at the tail end of the Roaring Twenties and became one of those rare songs that functions as a piece of advice. Crooner Seger Ellis recorded it first in 1928, but it was Louis Armstrong who made it immortal a year later. Satchmo’s 1929 recording turned a pleasant Tin Pan Alley tune into a jazz standard — he stretched the phrases, leaned into that gravelly warmth, and played a trumpet solo that sounds like sunshine itself. He loved the song enough to record it at least three times across his career, in 1929, 1932, and 1956.

From there it became a permanent fixture of the American songbook, recorded by Duke Ellington, Billie Holiday, Frank Sinatra, Judy Garland, Dean Martin, Louis Prima, and of course Nat King Cole, whose velvet-smooth reading is many listeners’ favorite — all warmth and effortless swing, the sound of a man who means it. One of the songwriters, Larry Shay, went on to become a music director at MGM, where he gave a young Bing Crosby his first movie job at fifty dollars a day. And the song has traveled further than anyone could have guessed: since the 1980s it’s been the beloved terrace anthem of England’s Leicester City Football Club, sung by tens of thousands of fans at once. Nearly a century on, the premise still holds up — smile, and the world smiles back.