Williams also executive produced the Lifetime biopic Aaliyah: The Princess of R&B, which premiered on November 15, 2014. In September 2015, the documentary series Death By Gossip with Wendy Williams premiered on the Investigation Discovery channel, both hosted and produced by Williams.
Before Wendy turned 50, stand-up comedy was on her bucket list. In 2014, Lipshtick called Williams to participate in their first all-female-based comedy series at the Venetian in Las Vegas. Williams made her sold-out comedy debut on July 11, 2014. Williams' comedy tour was called "The Sit-down Comedy Tour." Williams returned to Lipshtick on October 31, 2014, and November 1, 2014, after she made a sold-out debut in July.
Williams hosted her "How You Laughin'" Comedy Series at NJPAC on November 15, 2014, featuring Luenell, Jonathan Martin, Pat Brown, Hadiyah Robinson, and Meme Simpson. In 2015, Williams announced a 12-city comedy tour called "The Wendy Williams Sit Down Tour: Too Real For Stand-Up."
In 2014, Williams and two others produced a biopic on the early 2000s R&B artist Aaliyah, entitled Aaliyah: The Princess of R&B. The biopic attracted much controversy as Aaliyah's family neither consented nor authorized the use of Aaliyah's image or her material for the biopic. The film also romanticized the hebephilic relationship and subsequent illegal marriage of the young singer and R. Kelly, who in 2019 was indicted of 10 counts of aggravated criminal sexual abuse, obstruction of justice, and 18 federal counts, including child pornography, kidnapping and forced labor, as of July 12, 2019. Critical reception to Aaliyah: The Princess of R&B was predominantly negative. Jon Caramanica of The New York Times panned the film, criticizing it as "ham-handed" and "underwhelming" and writing "Condensing the singer's life into such a short space requires a cruel knife and, in this case, a wildly imprecise one. A good film doesn't show its seams. This one — based on Aaliyah: More Than a Woman, a biography by Christopher John Farley — is mostly seams. Much of the acting has dull edges, and the screenplay is aggravatingly stilted." The Wall Street Journal also criticized the film, commenting that the "overuse of the three and four-way split screen montages only enhanced the lack of material." Viewer reaction for the film was similarly extremely negative, and fans mocked the film on social media websites, using the hashtags #LifetimeBiopics and #LifetimeBeLike.