The Grateful Dead and Uncle Sam have an interesting relationship. The band's followers, the 'Dead Heads', have produced a great deal of artwork, much of which features imagery related to Uncle Sam. Sam's trademark hat, in particular, appears in many examples of dead-head artwork. The hat often is worn by a skeleton.

Uncle Sam also appears in the lyrics of the Dead song 'US Blues'.

Since the band and its legions of followers have something of an anti-establishment flavor, some critics have suggested that the Dead's use of Uncle Sam imagery is insincere. One music critic referred to the Dead's use of Uncle Sam's hat as 'inspired mockery.'

Band member Bob Weir, however, has stated that the band has respect for Sam, 'he's up there with Marilyn Monroe and Paul Bunyan and people you may not know, James Dean, Otis Redding, the great ballplayers. We have our pantheon, and one of the figures in the pantheon is Uncle Sam. He's sort of like the godfather figure of American culture. So we actually have a fair bit of respect for him. And he comes around in different guises, you know - in our little region, he comes around as a skeleton, but he's still wearing the same hat.'

The lyrics to US Blues