Madonna is one of those artists whose songs are so baked into pop culture, you can probably sing along to several of them without even thinking about it.

From “Like a Virgin” and “Material Girl” to “Vogue,” “Holiday,” “Ray of Light,” and “Like a Prayer,” she’s spent decades turning out hits that defined entire eras of pop music. But while fans have their own favorites, the Queen of Pop herself has occasionally weighed in on which tracks she actually loves revisiting—and which ones she’s more than ready to retire.

Let’s “strike a pose” and take a look at Madge’s favorite and least favorite Madonna songs.

Madonna’s Favorite Madonna Songs

Madonna hasn’t exactly stuck to one neat list of favorites. Instead, her answers tend to shift depending on when and who is asking.

In a 2005 interview with CBS News, she was asked to name her favorite songs among her biggest hits. Without much hesitation, she picked “Holiday.” When reminded that the song only reached No. 16 on the Billboard Hot 100, she still stood by it. The 1983 track, after all, was the one that helped introduce her to mainstream audiences and kick off her pop career in earnest.

She also named “Like a Virgin,” “Material Girl,” and “Like a Prayer” in the same conversation. At the time, these weren’t just chart hits—they were the songs that turned her into a global pop fixture in the 1980s, whether she liked that framing or not. “Like a Prayer” in particular has continued to stand out in her catalog. Released in 1989, the track leaned hard into gospel-pop territory, but it was the music video that actually caused the controversy. After the dust settled from the boycotts and the Vatican’s outrage, the song was finally seen for what it is: one of her most fearless and career-defining moments.

It’s no coincidence that Madonna wrote “Like a Prayer” in just three hours, and it’s a song that continues to stick with her to this day. In a 2015 interview on The Howard Stern Show, Madonna admitted some of her best songs come together in just a few hours, including “Vogue,” which she originally wrote for Dick Tracy. Despite the massive legacy of her solo albums, she’s remained surprisingly loyal to that era; when Q Magazine asked her to name the studio effort she was most proud of, her answer was characteristically contrarian: “I would have to say the favorite record that I’ve made is the soundtrack to Dick Tracy. I love every one of those songs.”

Today, if you asked the singer to identify her creative zenith, she likely wouldn’t point to the “Material Girl” era. Instead, she’s consistently championed her 1998 “rebirth,” Ray of Light. Following the birth of her daughter, Lourdes, and a spiritual awakening, Madonna traded her bubblegum pop for electronic soundscapes and introspective lyrics. She has frequently cited the haunting standout track “Frozen” as a personal favorite, largely because it allowed her to show off the expanded vocal range she developed while filming Evita.

Her pride extends to her visual work, too. While she spent decades defending the grainy, black-and-white hotel escapades of “Justify My Love”—famously taking to Nightline in 1990 to argue that her “experimental” work was being unfairly censored—she recently named a new champion. In a 2022 career retrospective, she crowned the lush, cinematic bullfighting drama of “Take a Bow” as her personal favorite music video.

Madonna’s Least Favorite Madonna Songs

For someone with a catalog this large, you might expect hesitation when asked about least favorites. Madonna hasn’t really shown much of that.

In a 2015 interview with Us Weekly, she was blunt when asked to name the song she could do without: “Material Girl.” “I never want to hear it again!” she declared. The 1985 hit became one of the defining songs of her early image—so much so that it essentially stuck to her public persona for decades afterward.

She’s also joked in other interviews about being less than enthusiastic about revisiting “Like a Virgin,” another early signature hit, largely because of how often it has followed her throughout her career and touring life. That fatigue, according to Madonna, isn’t necessarily a critique of the songwriting, but a byproduct of sheer overexposure. After forty years of hearing her own voice echoing through every airport terminal and hotel lobby on the planet, she admits that some of her biggest hits have lost their luster.

At one point, she even remarked that she’s heard some of her songs “five billion times,” which probably says it all.

Express Yourself—Even If You Hate the Song Later

Like most artists with a four-decade career, Madonna’s relationship with her own catalog isn’t static. Songs that once marked radical breakthroughs can eventually become heavy with the weight of expectation and repetition.

For fans, these tracks are often preserved in amber: anchored to a first dance floor moment, a road trip, or a specific phase of life. But for Madonna, those meanings have naturally shifted; what once felt like a bold new frontier has, in some cases, become a house guest she’s lived with for forty years.

This friction between the public’s nostalgia and her own creative restlessness is what keeps her work interesting. Whether she’s currently championing a track as a personal favorite or admitting she’s completely over it, those songs remain the foundational architecture of modern pop.

They serve as a reminder that even the most iconic art is never truly “finished”—it continues to change, both for the audience that listens to it and for the woman who wrote it in a three-hour whirlwind decades ago.

Learn More About Iconic Artists’ Least Favorite Songs: