20. King Henry VIII
Approximate Weight: 200 lbs.
The man who separated church and state—and was known for multiple marriages—was like the original celebrity scandal. His pride and personal vanity is why he strived to make a male heir, but it also resulted in some pretty exquisite looking garb. While no photos exist, he certainly looks like a boss in all his portraits. Leggings aside, his regal fur and patterned garments look luxurious as hell, and he was also known for wearing a noble "cap of maintenance"—often made from velvet and lined in ermine (that's short-tailed weasel for you peasants). To top it off, with that facial hair, he looks like Action Bronson's ancestor.