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Winning Uglyby The Rolling Stones
And we’re heading for the heartbreak/ Heading for the blues..
Written by: Jagger/Richards Recorded: RPM Studios, New York, USA, July 16-Aug. 17 1985; Right Track Studios, New York, USA, Oct-Decx. 1985 Guest musicians: Chuck Leavell (synthesizer), Janis Pendarvis and Dolette MacDonald (backing vocals) *Data taken from Martin Elliott’s book THE ROLLING STONES COMPLETE RECORDING SESSIONS 1962-2012
Winning Ugly stands as one of Mick Jagger’s main contributions to Dirty Work, along with Back to Zero. The song’s tone is steeped in cynicism, portraying a protagonist willing to go to any lengths to succeed, even if it means rigging the competition. It’s a perfect opportunity for Jagger to launch another critique against those who lust for power, as he sings in the first verse: “I never turn a hair, just like the politicians.” This blunt cynicism is underscored by a sort of internal conflict—almost a split in identity. Behind the scenes, back in the dressing room (is this character perhaps an artist?), a different side of him mourns the hollow victory. Winning Ugly also reflects the complex dynamics between Mick and Keith, which might explain why it’s never made it onto the setlist for Stones’ tours to this day.
In Winning Ugly the Rolling Stones’ foundational sound is almost unrecognizable. While the track is competently executed, it leans heavily into an ’80s aesthetic, coming off somewhat like a Duran Duran imitation—perhaps influenced by visits from members of that band during Dirty Work sessions. From the intro onward, the song unmistakably announces its ’80s vibe, complete with the era’s notorious production quirks. Despite John Regan’s solid bassline and Charlie Watts’ powerful drumming, Chuck Leavell’s synthesizer work—layered over Keith’s guitar chords—bears a resemblance to the lackluster production styles that defined much of the decade’s pop landscape.
The sound of Winning Ugly reflects the FM radio trends that dominated the airwaves worldwide during the ’80s. Unfortunately, the Stones seem to have been swept up by this mainstream style. Although Keith Richards has mentioned that the song’s riff was inspired by Marvin Gaye classics like Stubborn Kind of Fellow, You’re a Wonderful One and Can I Get a Witness, the track doesn’t strongly convey Motown’s spirit. However, Keith’s guitar lick stands out as a redeeming feature. It’s deceptively simple but has challenged many guitarists who’ve attempted to play it—a testament to Keith’s distinctive touch.
Guitar technician Alan Rogan explains that Keith Richards used Ron Wood’s blond 1959 Fender Telecaster to play the riff on Winning Ugly. Ronnie added his own rhythm guitar part, with both guitarists layering in additional elements to enrich the track. Mick Jagger, however, delivers his performance with little inspiration, seemingly restless and exploring potential directions for his solo career. This lack of enthusiasm is palpable, hinting at his desire to branch out creatively beyond the confines of the band.
Two extended versions of Winning Ugly were released as 12-inch singles, titled the London Mix and the NY Mix. These versions offered a longer, more detailed exploration of the track, showcasing the Stones’ attempt to tailor their sound to diverse audiences and enhance the song’s reach during the ’80s era of remix popularity.
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