Madonna and Brother Christopher Ciccone’s Complicated Relationship: A Look Back

Madonna and her younger brother Christopher Ciccone had a relationship full of ups and downs, with Christopher going from her collaborator to estranged family member over the decades until his death in 2024.

Christopher’s family confirmed to Us Weekly that the dancer, author and interior designer had died of cancer on Friday, October 4, in Michigan surrounded by family, including his husband, Ray Thacker. He was 63. Christopher was one of Madonna’s five siblings, which also includes brothers Anthony, who died in 2023, and Martin, and sisters Paula and Melanie. (They also have two step-siblings, Jennifer and Mario.)

After following her to New York City in the 1980s, Christopher worked for his sister as a backup dancer, dresser and, eventually, her tour director for The Girlie Show in 1993. However, Madonna’s rise to fame ultimately soured their relationship, creating distance and resentment. In a 2008 interview with Good Morning America, Christopher shared that previously he and Madonna “were a very close brother and sister,” and said that it felt “a bit like a marriage.”

Madonna mourned her brother’s death via Instagram, calling Christopher “the closest human to me for so long,” in her tribute. “It’s hard to explain our bond,” she wrote. “But it grew out of an understanding that we were different and society was going to give us a hard time for not following the status quo.”

Keep scrolling to read all about Madonna and Christopher’s ups and downs throughout the years:

1980s

Christopher was very involved in the early years of his sister’s career as a dancer, a dresser and a creative consultant. He shared in his memoir, Life With My Sister Madonna, that he had moved to New York City in the 1980s to be her backup dancer, even appearing in the music video for her single “Lucky Star” in 1984.

In an interview with The Guardian, Christopher confided that he, at times, found working for his sister to be “beneath” him after developing his own career in New York as an artist. “I did it because she needed me, but it bred resentment,” he claimed at the time. “Not many people would have been able to deal with her stuff.”

1990 – 2001

In 1990, Christopher was the art director for Madonna’s Blond Ambition World Tour, returning in 1993 as her tour director for The Girlie Show. However, the “Like a Virgin” singer looked outside the family for the Drowned World Tour in 2001, hiring choreographer Jamie King as director instead. It was around that time that Madonna married Guy Ritchie, who Christopher claimed further strained his relationship with the pop star. (Madonna and Ritchie split in 2008.)

1991

Christopher cited the 1991 documentary Madonna: Truth or Dare as an issue between him and his sister, though he hadn’t brought it up to her at the time the film was being made.

“At one point, if you’ve seen the Truth or Dare movie, when she’s rolling around on my mother’s grave that — that was a turning point for me in my relationship with her,” Christopher told Good Morning America in 2008. Madonna and Christopher’s mother — also named Madonna — died of breast cancer in 1963.

“I kept it inside but I thought to myself, ‘OK, there are no boundaries now.’ You know, my mother’s now become a side — a bit player in her life, life story, and it hurt me,” he added. “My opinion of her altered at that moment. I never said anything about it.”

2008

Christopher released his tell-all autobiography detailing his relationship with the pop icon, which became a New York Times best-seller and led to speculation that he and Madonna were not on good terms.

Madonna’s rep Liz Rosenberg told AP at the time that she hadn’t read the book but found it “very upsetting” that Christopher had “decided to sell a book based on his sister.” Four years later, Christopher doubled down in an interview with CBS News, saying he didn’t “regret” writing the book.

“It gave people an opportunity to think of me as a creative person, as an artist and not just as Madonna’s brother, which is a tag I’m going to wear forever,” Christopher said in 2012. “But I’m hopeful that at some point it will be Christopher Ciccone first. It’s cool … I’m perfectly happy being what I am.”

2012

In an interview with The Standard, Christopher shared that his relationship with Madonna was on a “perfectly personable level right now,” adding, “As far as I’m concerned, we’re good.” He said, “We are in contact with each other, although I haven’t seen her for a long time. We’re back to being a brother and sister. I don’t work for her, and it’s better this way.”

2023

Christopher and Madonna’s oldest brother, Anthony Ciccone, died of respiratory failure and throat cancer. He was 66.

2024

Madonna mourned Christopher’s death via Instagram on October 6, sharing a series of photographs of the two siblings throughout the years.

“The last few years have not been easy,” she wrote in a long, heartfelt caption. “We did not speak for some time but when my brother got sick. We found our way back to each other. I did my best to keep him alive as long as possible. He was in so much pain towards the end.” She concluded, “I’m glad he’s not suffering anymore. There will never be anyone like him. I know he’s dancing somewhere.”