Gambling turns dangerous for Oliver on the Smallville episode titled "Roulette." That's a lesson for you, kids.
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Steph Song, as Victoria, causes problems for Oliver on Smallville. This photo is taken from the episode "Roulette."
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Oliver is seen here in a scene from Supernatural. He's seen better days than those during season nine.
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Smallville Season 9 Episode 5 Quotes

Clark: I hope I have enough detergent. How do you even have anything left to wear?
Lois: You know, most guys wouldn't complain if I suddenly found myself shirtless.

Lois: About time you got home. Shelby's great and all, but the conversation... a little one-sided.
Clark: Shouldn't you be riding a mechanical bull somewhere? It is Friday night.