"Vanilla Twilight" is the second single from Owl City's second album Ocean Eyes. The song is about Adam Young's high school girlfriend, who moved away. The song features both piano and synthesizer instrumentation. The music video for "Vanilla Twilight" premiered on March 24, 2010. It features a cameo by Shaquille O' Neal. The video was directed by Steve Hoover and was filmed on location in Pittsburgh, PA.

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