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Sydney was booked for her first ever shoot for "Playboy's Sexy Girls Next Door", one of the Special Editions. After that, she just kept getting called to shoot more and more for Playboy, and each time she had more and more fun. Later her work expanded to include doing Playboy videos (like Playboy Wet & Wild: Slippery When Wet (2000) (V), Playboy: Girls of Hedonism, Runaway Bay Jamaica (2000) (V), Playboy: Wet & Wild Live! (2002) (V) and Playboy: No Boys Allowed, 100% Girls 2 (2004) (V)), shows on the Playboy Channel.