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Warning: major spoilers for the second episode of Season 4 of Arrow ahead.
The second episode of the fourth season of Arrow – innocuously entitled “The Candidate” – saw an awful lot of stuff happen. Oliver decided to run for mayor, Laurel celebrated the anniversary of Sara’s death by digging her up, Felicity tried her hand at C.E.O., but all is trivial in the grand scheme when the biggest twist of the night is considered. Oliver’s return to Lian Yu in the flashbacks saw something so monumental that it pretty much eclipses everything else that has happened in the flashbacks since…well, ever. In order to infiltrate the latest group of bad guys to take up residence on Purgatory, Oliver dons a set of camo and gets most of his hair chopped off, which really translates to one major thing for the future of the series:
Ding dong, the wig is gone!
Finally, after three seasons and one premiere of Flashback Ollie rocking wigs that were somehow harder to watch than the hero losing his soul and descending into darkness, Flashback Oliver looks like an actual past version of present Oliver rather than a random guy trying to single-handedly make hobo chic a thing. Still, losing the tangled mop on his head is a big change for Oliver. So, let us take a moment to reflect on the long, arduous journey of Oliver’s flashback hair.
Arguably the worst wig of the lot was the original recipe Ollie wig that somehow made him look like either a smarmy douchebag – for there is truly no better word for it – or a serial killer. It worked for the Ollie character who had taken his girlfriend’s sister off on a sex cruise, but it was also terribly hard to look at without wanting to smack him in the face and tell him to think about his life decisions
The island wig had its charms, insofar as the island setting somewhat justified the monstrosity on his head. In fact, if we take the hair of each of the three characters living in the fuselage as representations of their survival instincts, of course Oliver’s hair would look like a scraggly dead animal while Slade and Shado look fetching.
The Hong Kong wig was the most objectionable. Oliver was back in civilization, living in a household of three other people with presentable hair. Tatsu was a master swordswoman who probably would have loved to wave shears around Oliver’s head in the first half of Season 3. Sure, she might have slit his throat for his uselessness at household chores, but at least he'd be presentable in death.
Honestly, it was bad enough that the big blond white guy was lumbering around the city trying to be incognito, but sticking a baseball hat on him and sending him stateside was so much worse.
Flashback Oliver jumping around rooftops in the Season 4 premiere did finally give some clarity on one peculiarity of his character. The impracticality of a hood for a style of fighting that requires peripheral vision has always been a sticking point, but the flashbacks made it clear that the hood was not so much a deliberate choice in the present as a muscle memory from a past when his hair was so bad that he would not even subject criminals to it.
Rest in peace, Flashback Wig. You won’t soon be forgotten.