Oprah once asked the 'Teenage Mutant Ninja Turtles' about interspecies dating — and instantly regretted it
Throughout television history, only a few individuals are widely regarded as true legends. One of those people is Oprah Winfrey, who is considered one of the greatest talk show hosts of the 1990s and beyond. During the peak of Winfrey’s career, the 'Teenage Mutant Ninja Turtles' were also at the height of their popularity. Years before Megan Fox starred in their films, the Turtles had the opportunity to share the spotlight with Winfrey. However, their interview with her ended up being quite awkward.
A full, high-quality version is not widely available. A low-quality YouTube video exists, capturing several minutes of the interview, but the sound is poor, and the visuals are heavily distorted. Another short YouTube clip, about 40 seconds long, provides a clearer version of a particularly infamous moment from the interview. Although this clip is still of low quality, the dialogue is easier to understand. In the beginning of this video, Winfrey asks, "Do you sometimes wish that April O'Neil was a turtle?" This question was innocent enough, but the response that followed was unexpected. The actor portraying Raphael responded, "Oprah, I've been trying to talk her into an interspecies relationship for months now," as reported by AV Club.
As unsettling as that comment was, the conversation took an even stranger turn when the performer playing Michelangelo added, "The main problem is she can't hold her breath long enough." While this statement could have an innocent meaning, it also carried an uncomfortable implication. The camera then cut to a young audience member whose facial expression showed clear discomfort. This reaction became widely recognized and was even used as a joke in Screen Junkies’ honest trailer for 'Coming Out of Their Shells.' Over time, this particular interview has gained a reputation for being one of the most awkward moments in television history.

At times, certain pop culture trends capture the public's attention in a big way. In the early 1990s, the 'Teenage Mutant Ninja Turtles' did just that, becoming a favorite among an entire generation of kids. Their animated series first premiered in 1987 and was later picked up by CBS. The show went on to run for ten seasons, producing nearly 200 episodes—an impressive achievement for any animated program. Alongside the animated series, there was a booming market for Turtles merchandise. Countless action figures based on the show’s characters were sold, and it seemed like any character featured in an episode could get its own toy. The first live-action 'Teenage Mutant Ninja Turtles' movie hit theaters in 1990 and became a major success. This only fueled the Turtles' popularity, even attracting adult fans to the franchise.

Evidently, one of daytime television’s most famous hosts saw an opportunity in the Turtles’ popularity. Winfrey agreed to interview the performers from the 'Coming Out of Their Shells' stage show while they were in full costume. Bob Bejan, one of the album’s co-writers and the live show’s writer and producer, was interviewed for the GameSpot article. He reflected on how incredible it was that Winfrey hosted the Turtles on her show, stating, "When you think about the fact that we convinced Oprah Winfrey to do an entire hour like that. Like, that's wild. Because it wasn't like she was a nobody; she was huge by then already." But no matter how memorable their interview was, it was also equally cringe.