most haggard looking musician

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Even Merle ain't that haggard.
 
It's probable that Keith Richards didn't need any makeup for the "Pirates" movie.

& The Igster is definitely a close 2nd.

Janis Joplin: Nominee for "ugliest man on campus", University of Texas, 1963.

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Ronnie Wood looks really rough.

Ginger Baker and Jack Bruce from Cream

Guys like Clapton, Ringo, and Townshend/Daltrey made out ok
 

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