She went on to become the first woman to hold a morning drive time position on AM radio in a major market when she replaced Don Imus at WNBC in New York City in 1977.

[5] Dylan later established Skyshapers University and Sky U to develop and produce multimedia programs to motivate elementary school-age children to excel.

[6] Subsequently, Dylan produced and co-directed the feature documentary, On Our Own Island, which received many accolades and screened at film festivals around the world.

(This professor later bestowed the honor of Phi Beta Kappa on Dylan upon her graduation in the top percentile of her class at Tulane in 1974.)

[11] There she posed pointed questions to the likes of David Duke, Grand Dragon of the KKK, and Lester Maddox, controversial Georgia Governor, who is reported to have walked off her show.

[13] By June of that year, Dylan was on the cover of the Chicago Tribune Sunday Magazine, which called her "82 pounds and 50,000 watts of down-home disc jockey."

Although Imus had a loyal following, Dylan in her first rating book increased WNBC's morning audience, and became the most listened-to female disc jockey in the United States.

Drawing from her past when she was discouraged from becoming a radio disc jockey and then a television host/producer, only to succeed at both, Dylan next set her sights on developing entertainment to motivate children.

[18] By August 1988, Dylan had also formed a 501(c)(3) public charity, the Skyshapers Foundation to develop and distribute children's motivational programs and scholarships.

[21] In excess of 14 million pieces of Skyshapers materials were distributed to fulfill orders from 10,000 public and private elementary schools, and thousands of Boys' and Girls' Clubs, Scout troops, and church- and synagogue-affiliated youth groups in the United States.

There is truly a void in hip, solid entertainment with a positive lifestyle message...that gives children action steps, rather than a slogan, to achieve excellence and reach their dreams.”[17] In 2022, Dylan completed and premiered the feature documentary, On Our Own Island, a timeless true love story that chronicles the seasons of a relationship from its romantic beginnings through life’s final moments.

The film was inspired by and dedicated to Dylan’s husband of 33 years and Sky’s father, Steven Robbins, who died in February 2016.