A lithe, long-haired blonde actress who made the most of her expressive eyes and smile, Leslie Grossman pushed down her desire to act through high school and college, instead choosing to focus on academic pursuits. Working behind the scenes in theater productions in high school, the California-raised Grossman was convinced to act in a production while attending Sarah Lawrence College in New York, and eventually appeared Off-Broadway in that same play, a soap opera spoof entitled "Cereal!" which chronicled the ups and downs of a family of dry cereal tycoons with odd names. Grossman, who played a character called 90210, headed back west following this production, and went on to land a TV guest role in the UPN series "Guys Like Us" and a cameo in the feature "Can't Hardly Wait" in 1998.
Like many of the performers cast on the comedy-drama teen series, Grossman was looking for her breakthrough and found it on "Popular" (The WB, 1999-2001) playing Mary Cherry, an ebullient and slightly odd rich girl with a smile that would seem sweet if one didn't know her wicked ways. Less concerned with maintaining the regulations of the holy order of popularity and more prone to self-promotion than co-villain Nicole, Mary Cherry pulled no punches on her way to the top, showing off her wealth with ridiculous displays and daring to even cross head cheerleader Brooke (Leslie Bibb). Unexplained flickers of humanity like her championing of Carmen (Sara Rue), an overweight but talented cheerleader candidate, made her all the more peculiar. Some of the character's eccentricities were explained when her mother Cherry Cherry (Delta Burke, in a recurring stint), a colorful oil baron landed in town. Grossman and Burke, both actresses who obviously enjoy their work, had great chemistry, and the storyline put the too frequently overlooked character of Mary and her formidably talented portrayer in the forefront.