Oshima was relocating to Miami Beach from Playa del Carmen, Mexico where she was living and working. Through a mutual acquaintance she met Playboy photographer, Jarmo Pohjaniemi. Oshima stated in her Playmate appearance interview, "I could never have been a model in Japan. I would be considered too busty." After her discovery, she was brought to California for a test shoot as a candidate for The 50th Anniversary Playmate Hunt in the December 2003Playboy, her first magazine appearance was the pictorial of models auditioning. In addition to her Anniversary Playmate search pictorial, she also made several appearances in other Playboy editions. Oshima was the covergirl of the 2003 Playboy Special EditionsExotic Beauties and she has also starred in a number of Playboy videos. In June 2004, she became the second Japanese-born Playboy Playmate. The first Japanese-born Playmate was Lieko English who appeared in the June 1971 issue of Playboy. She appeared in the 2005 Playmates at Play at the Playboy Mansion swimsuit calendar as the January calendar girl. The calendar was the inaugural Playmates at Play calendar and was shot on the grounds of the Playboy Mansion in 2004. It was the magazine's first attempt at creating a non-nude swimsuit calendar featuring Playmates similar in style with those from the Sports Illustrated swimsuit issue. While all Playmates appeared in bikinis in the calendar, only Oshima and Karen McDougal appeared in painted-on bikinis. She has also been listed as a Photo Production Coordinator in various issues of Playboy Special Editions.
Appearances
Prior to her Playmate appearance, Oshima appeared in the music video for Nelly's "Shake Ya Tailfeather" and in the Beyoncé-Lady Gaga video for their single Telephone. She also appeared in several episodes of The Girls Next Doorreality show on the E! network. She was cast as herself in the 2008 motion picture The House Bunny, and was also in the 2009 motion picture Race To Witch Mountain. Oshima has also appeared in the television comedy series Community, and in 2013, the comedy feature filmDealin' With Idiots and the 2015 motion picture The Wedding Ringer. In 2011, Oshima was featured in a print ad/billboard advertising campaign for Virgin America. In 2017, she was featured in MGMT's music video for the song Little Dark Age.
