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Over 100 episodes of Arrow, Oliver Queen (Stephen Amell) has been striving to save his city as the Green Arrow, and looking good while doing so. However, not all of the expert archer’s fashion choices have hit the target.
Throughout the show’s five seasons, Arrow fans have watched Oliver’s evolution toward becoming Star City’s resident hero via flashbacks, in which the playboy-turned-vigilante dons a number of hairstyles, to varying degrees of success.
ET’s Leanne Aguilera spoke to Amell and other stars from the CW superhero hit at Arrow's 100th episode celebration in Vancouver last month, and got them to weigh in on some of Oliver’s more interesting ‘dos. Check out the video above for their hilarious reactions!
Queen’s Gambit Oliver, aka The Frat Boy 101

“He looks so sweet!” David Ramsey, who plays John Diggle, gushed of pre-shipwreck Oliver. “Playboy Stephen in one of many wigs.”
“I was seducing Sara Lance (Caity Lotz) and that’s the haircut you needed,” Amell said with a laugh.
Echo Kellum, who joined the Arrow cast as Curtis Holt/Mister Terrific in season 4 and therefore missed out on a lot of great early-Oliver hair, wasn’t quite as convinced. “What I see here is a hairline that couldn’t exist truly in real life,” he quipped.
New-to-the-Island Oliver, aka The Douche Out of Water

Fresh off the boat, and stranded on Lian Yu, this Oliver look is a slightly-disheveled variation on the first. “That’s like, I’ve been through some stuff,” Kellum observed.
Emily Bett Rickards, who plays Felicity Smoak, likened the ‘do to “Tarzan,” while Ramsey got more of a Zoolander vibe.
“Those are eyes of steel right there, am I right?” he joked. “That’s Blue Steel, baby!”
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Long Hair Oliver, aka The “New Bachelor”

Colton Haynes, who played Roy Harper on Arrow’s first three seasons, had the most fun with this hairstyle, comparing the “new Bachelor” look to both Brad Pitt’s long locks in Legends of the Fall and Chord Overstreet’s shaggy ‘do on Glee.
Ra’s al Ghul Oliver, aka The Bad Boy Buzzcut

While Oliver’s turn as the head of the League of Assassins in season 3 was a dark point in his character arc, it led to an undisputed haircut highlight for the whole cast.
“Stephen, I think you look the hottest with this hair!” Haynes told Amell, who agreed that the look was a favorite of his.
“Oh, I like that,” Kellum added. “You don’t want to mess with a dude with short hair.”
Clean-Cut Politician Oliver, aka The “Mayor Handsome”

“Oh, that’s smooth! Big Daddy right there,” Ramsey said with a laugh. “That’s the guy I met and fell in love with right there. That’s my boo-boo.”
“I just think it’s really hot,” Haynes agreed.
End-of-the-Island Oliver, aka The Full-On Cast Away

Finally, the ultimate Oliver look has only been seen briefly in Arrow's first season, when Oliver is rescued off of Lian Yu after five long years. However, Amell teased that the long, tangled hair and unkempt beard will be “see again soon!”
“Look at the eyes,” Ramsey added. “Look at the steely eyes and the hair. He knows something.”