I'm
Button promoting the National Rifle Association from last year's election.

Pop
Said to be a button for a rock group.

Heidi
North Dakota attorney general Heidi Heitkamp was the Democratic nominee for governor in 2000.

Saylor
John Saylor was a veteran GOP member of the House from Pennsylvania until his death in 1973.

Man
Well, this person is clearly a man. But I don't know anything else about him. Anyone have a clue?