Apple sang with Johnny Cash on a cover of Simon & Garfunkel 's `` Bridge over Troubled Water '' that ended up on his album American IV : The Man Comes Around and was nominated for a Grammy Award for `` Best Country Collaboration with Vocals '' .
Apple sang with Johnny Cash on a cover of Simon & Garfunkel 's `` Bridge over Troubled Water '' on Cash 's 2002 album American IV : The Man Comes Around .