Written and first recorded by Ruthann Friedman (1967).
Hit versions by The Association (US #1/CAN #1/UK #34/AUS #53/NZ #6 1967), Wes Montgomery (US #44/MOR #10 1967).
From the wiki: “‘Windy’ was written by Ruthann Friedman, a transplanted New Yorker who moved to Venice, California, where she hung out with the cream of L.A. Pop royalty – a 16-year-old sneaking into the Troubadour in the early ’60s and, then, an 18-year old starting to write and play her songs on the guitar, making friends with David Crosby, Van Dyke Parks, and Tandyn Almer, author of ‘Along Comes Mary’, another big hit for The Association.
“Friedman later recalled ‘I just was bopping around playing music with my friends, going to San Francisco, staying with friends up there, staying down here in Los Angeles. It was kind of a gypsy life that a lot of us led. Honestly, I just felt this is what I expected to happen. It’s what I anticipated would happen.’
“Friedman remembers writing ‘Windy’ in about 20 minutes while living in an apartment in Crosby’s house. ‘People said it was about my hippie boyfriend up in San Francisco. I never had a hippie boyfriend. These days, looking back at myself in my mid to late 20s, I finally realized I was talking about me in that song, and how I wanted to be.’
“Friedman was introduced to the Association by their mutual friend, Beach Boys lyricist Van Dyke Parks. It was producer Bones Howe who changed the tempo of ‘Windy’ to a common 4/4 beat, believing that doing so would increase the song’s commercial appeal. The Association’s recording session proved grueling, starting in the early afternoon and ending around at 6:30 a.m the next morning (after which the group had to make an 8:30 a.m. flight to a live performance that evening in Virginia). Because of the poor showing of their last album Renaissance, on which the Association performed all their songs, Howe had session musicians (the Wrecking Crew) substitute for the sextet on their third album, which included ‘Windy’, in order to get a radio-friendly sound.
“Later in 1967 an instrumental version by jazz guitarist Wes Montgomery became his biggest Hot 100 hit when it peaked at #44, and #10 on the Easy Listening chart.”
The Association, “Windy” (1967):
Wes Montgomery, “Windy” (1967):