John Leguizamo recently shared a fascinating anecdote regarding his past connection to pop icon Madonna, revealing that her then-husband, Sean Penn, once disclosed that she had feelings for him. This revelation emerged during an appearance on Kelly Ripa’s podcast, *Let’s Talk Off Camera*, where the actor recounted his experiences with the singer and their mutual friends from years gone by.
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The story dates back to 1984 when Leguizamo made a cameo as an extra in Madonna’s “Borderline” music video. Although he was part of one of her breakthrough projects, he did not actually meet the singer at the time. Years later, while filming *Casualties of War*, Leguizamo was surprised to hear from Penn—their co-star and Madonna’s husband—about her supposed crush on him. “She married Sean Penn. We were doing Casualties of War, and Sean told me that she had a crush on me,” he recalled.
Leguizamo had high hopes that appearing in the “Borderline” video would lead to greater opportunities, especially having heard that Madonna had an interest in Latin men. He reminisced about showing up to the shoot with a mindset akin to “Cinderella,” believing he could somehow catch her attention. Unfortunately, his experience was far from glamorous; he found himself assigned to a background role, leaving him to return home with nothing more than a sandwich.
Around the time of the music video’s release, Madonna had already begun dating Sean Penn after they met while filming the “Material Girl” music video in 1985. Their romance escalated into marriage later that year, making headlines across the globe. However, the couple’s relationship was tumultuous, with Madonna filing for divorce multiple times before the marriage came to an official end in 1989.
During the filming of *Casualties of War*, Penn, having been privy to Madonna’s past feelings for Leguizamo, shared this details during a conversation with him. Though both individuals were otherwise occupied—Madonna married and Leguizamo involved with someone else—the revelation added an amusing twist to Leguizamo’s memories.
With time, Leguizamo’s relationship with Madonna evolved into a more amicable one. He recounted enjoying dinners with the superstar in both London and Manhattan, often in the company of other notable figures, such as musician Lenny Kravitz. He painted a picture of such gatherings as informal evenings among friends, typically commencing around 8 or 9 PM.
In a light-hearted tone, Leguizamo added that he would wholeheartedly accept an invitation to collaborate with Madonna again, should she ever reach out. “Hell yeah,” he quipped, expressing his enthusiasm for the prospect of appearing in one of her future music videos.
Currently, Leguizamo is busy with several projects, including his role as Eumaeus in Christopher Nolan’s adaptation of *The Odyssey*, which was released this past July. He also has a part in Mike Flanagan’s upcoming horror film *The Exorcist* and is negotiating a reunion with Matt Damon for an untitled project with the Daniels. Additionally, fans can expect to see him return as the voice of Sid the Sloth in the upcoming animated feature, *Ice Age: Boiling Point*, due out in February 2027.
Overall, Leguizamo’s memories and anecdotes not only offer a glimpse into the interconnected world of Hollywood but also highlight the intriguing intersections of personal lives and professional paths. Whether reflecting on past experiences or looking ahead to exciting new roles, it is clear that the actor remains an active and engaging figure in the entertainment industry.