Madonna Doesn't Hold Back Disdain For Her Famous Failed Marriages

Over the last four decades, Madonna has made just as many headlines for her candor as she has for her extensive musical catalogue. Sometimes, this outspokenness has landed the "Material Girl" singer in hot water. You know, like the time she said she thought about "blowing up the White House," per Reuters, or when she shared her controversial opinions about COVID-19, according to The Guardian. Despite any potential fallout, the singer-songwriter has always retained her penchant for being an open book. 

Take, for example, the star's most recent YouTube video, entitled, "Finally Enough Talk: 50 Questions With Madonna." Over the course of nearly seven minutes, the famed songstress snappily answers a host of juicy questions as she strolls around her property. And while the video is packed to the brim with interesting tidbits, it's her revelations about her marriages that has set social media ablaze. 

For the record, Madonna has been married twice in her life. The first was with actor Sean Penn, who she was married to from 1985 to 1989. Decades later, Madonna married again. This time her groom was director-producer, Guy Ritchie. The marriage lasted from 2000 to 2008. And although much time has passed since both relationships fizzled out — and each party has gone on to enjoy relationships with other people — Madonna still hold some pretty strong opinions about her former marriages. 

Here's why Madonna likely regrets her marriages

During Madonna's video, the interviewer asks, "What's a decision you made that, looking back, maybe wasn't the best decision?" The "Vogue" singer, immediately responded, "Getting married," before adding, "Both times!" And while she didn't further elaborate as to why she feels this way in the video, previous interviews provide ample clues. 

For example, Madonna met Sean Penn on the set of her "Material Girl" video. Within six months, they were married. And while things were great for a time, sources close to the couple revealed, in the past, that jealousy and allegations of abuse, on Penn's end, led to the end of the marriage, per The Seattle Times. Despite the many ups and downs that Madonna faced with Penn, they're good friends today. In addition to working on charity projects together and Penn popping to support Madonna's 2015 tour, the actor also admitted her still loves her. "Ah, I love my first wife very much," Penn said (via Entertainment Tonight), when Stephen Colbert asked him to compare Madonna with Britney Spears. "There's no [comparison] ... you don't compare those things."

On the other hand, Madonna and Ritchie's marriage failed long before the public was made aware, according to People. During the piece, a source with purported information about famous couple listed a few things that led to their downfall, including distance, outside friendships, and differing religious beliefs. Unlike Penn, Daily Mail reports, Madonna doesn't appear to be close to Ritchie, with whom she shares two children..