Hercules Mulligan is one of Hamilton's most memorable supporting characters, but why does he wear a beanie at certain points of the musical? Created by and starring Lin-Manuel Miranda, the musical became a Broadway phenomenon after its debut in 2015, and replicated that success on Disney+. A large reason for that popularity is Hamilton's cast, which is made up of a diverse range of performers who each bring at least one historical character to life.
Okieriete “Oak” Onaodowan is one of the actors to play multiple parts, inhabiting Hercules Mulligan in Act 1 of the musical, before transforming into James Maddison for Act 2. Although it's the latter who is perhaps slightly more important to the story, forming a rivalry against Alexander with Thomas Jefferson (Daveed Diggs), it's Mulligan who is the far more popular of the two. That's not just because he's one of the good guys, but because of his iconic lyrics, including his unbeatable re-introduction in one of Hamilton's best songs, "Yorktown (The World Turned Upside Down)".
In several of his appearances prior to that number, Hercules Mulligan can be seen wearing a grey beanie hat - such as during the songs "Aaron Burr, Sir" and "My Shot", which stands out due to the fact it's quite obviously not of the time period Hamilton is depicting. The same can be said for the bandana Mulligan wears in other scenes, like the aforementioned "Yorktown", but it raises the question of why he wears a hat or bandana at all. The headwear wasn't initially intentional, but rather something that Onaodowan wore to rehearsals when it was a little colder outside, but that sparked off the idea of incorporating it into the show and playing into the character, given Hercules Mulligan is a tailor's apprentice. Speaking to the L.A. Times, Hamilton's costume designer Paul Tazewell explained:
"It seemed so connected to who Oak was as an actor, and I also thought that it connected him to Mulligan because it could live both in the 18th century and in the contemporary world. It gave him, as a tailor interested in clothes, a youthful, playful and more theatrical up-to-the-minute quality. So I thought it was a smart choice to incorporate that kind of thing in order to bridge the gap between their world and ours.”
It's certainly true that the beanie fits with what's presented of Hercules Mulligan's personality - he's presented as being among the coolest of Hamilton's characters, with a sense of swagger and, as Tazewell notes, youthfulness, and so him having the headwear fits nicely with that, but also the broader approach to Hamilton's adaptation choices, and not just in terms of aesthetics. The entire concept of the musical is that it is the story of America's past being told through the lens of America's present, which is why Hamilton features rap and hip-hop, and a cast of characters predominantly made up of people of color.
Beyond Mulligan's beanie, it's the meshing together of the then and the now in Hamilton is visible elsewhere in the costume choices. It may be more noticeable with the hat, but almost all of the performers are dressed in the clothes of the era from the neck down - the hairstyles, for instance, are allowed to remain much more modern, like with Diggs' natural hair as Lafayette, rather than having to wear wigs. This is then contrasted by King George, one of the few characters who does look old-fashioned even from the neck up, further cementing how he is part of the old world (hence why he is one of the only white characters), while the likes of Hercules Mulligan are part of Hamilton's new world.
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