Windy City

Osborne Brothers · Osborne Brothers 2 (1968-1974) [Bear Family] [1995]

(Bobby Osborne - Pete Goble)



We came to big city from our little country town

And every step she takes with you is down

But you're as cold and heartless as your chilling winds that blow

Before you freeze her heart please let go.



Windy City you're haunting my baby

With your bright lights and your avenues so wild

Windy City turn loose of my baby

If you don't give her back I lose my mind.



--- Instrumental ---



At night I walk your sidewalks and look in every bar

I love her even though she's gone too far

Your swinging doors stay open to keep her from my side

And I'm on your lonely streets again tonight.



Windy City you're haunting my baby

With your bright lights and your avenues so wild

Windy City turn loose of my baby

If you don't give her back I lose my mind...

Windy City - Osborne Brothers

The Osborne Brothers delivered a spirited rendition of "Windy City" on their 1968 album, capturing the quintessential sound of American country music during the late sixties. As one of the most celebrated bluegrass and country duos of the era, Bobby and Sonny Osborne blended traditional instrumentation with a polished, radio-friendly approach that defined their catalog. This recording reflects their signature style, characterized by tight harmonies and a warm, acoustic-driven arrangement that appealed to both country purists and mainstream audiences. Released on the Bear Family reissue series, the track stands as a testament to their enduring influence on the genre, showcasing their ability to reinterpret classic themes with fresh energy while maintaining the integrity of their roots. The song remains a staple of their discography, embodying the optimism and storytelling tradition central to their body of work.