She released nine singles and six albums between 1988 and 1991, including the number 1 hits “Boys” and “Gorgeous”. Her most recent album in 1995 (Femme Fatale) followed a hiatus following her marriage to music producer Toshinori Numata.

In July 2003, Sugimoto went through a high-profile divorce from her husband of 11 years. Sugimoto claimed that there was not enough sex in her marriage, and the term “sexless divorce” became a catch-phrase among frustrated wives in Japan. Sugimoto said, “I didn’t think it was such a big deal. I actually thought that it was a healthier reason for wanting out than a lot of other mud-dragging type of divorces.”

In 2004, she starred in director Takashi Ishii’s remake of Oniroku Dan’s S&M novel, Flower and Snake. Working with bondage master Go Arisue, she reprised the role first played by Naomi Tani in director Masaru Konuma’s version of the novel, Flower and Snake (1974). She spent approximately 75% of her screen time unclothed and participating in humiliating sexual acts but went on in the same year to be voted the second sexiest woman in Asia by Playboy magazine, beaten only by Zhang Ziyi.

In 2006 Sugimoto appeared alongside Japanese adult actress Sora Aoi in the midnight manga-inspired comedy-drama Shimokita Glory Days on TV Tokyo. The show also featured other adult actresses such as Yuma Asami in a story about a male college student moving to Tokyo and living in a shared house of women. Each of the twelve episodes were presented as ‘lessons’ which featured sexual themes and nudity. Sugimoto stated in an interview about the series that “society can’t consist only of ‘high-quality’ elements, and that’s also true for visual eroticism as well.”

In September 2008, Sugimoto became the first Japanese model in PETA’s international nude anti-fur campaign.

In November 2008 she performed a tango interpretation of the story of Sada Abe, a notorious prostitute who asphyxiated and castrated her lover. Titled Tango Nostalgia, the show was an extension of her performances on Nippon Television’s Urinari Geinojin Shako Dansu-bu (ウリナリ芸能人社交ダンス部, a Japanese TV show similar to Dancing with the Stars in which she performed with comedian Kiyotaka Nanbara.