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Britney Spears is one of numerous female pop stars who will be forever compared to Madonna. Fascinatingly, Spears said two of Madonna’s songs sound timeless to her. The two songs have nothing in common. 

Britney Spears called 2 Madonna songs ‘iconic’ in an essay she wrote for Rolling Stone

Rolling Stone ranked Madonna No. 36 on their list of the best artists of all time. As part of that article, the “… Baby One More Time” star explained why she admires the Queen of Pop. “Madonna was the first female pop star to take control of every aspect of her career and to take responsibility for creating her image, no matter how much flak she might get,” she wrote. “She’s proved that she can do so many different things — music and movies and being a parent, too. 

“Her music has become iconic: Songs like ‘Holiday’ or ‘Live to Tell’ are timeless — not just disposable hits,” Spears added. “They feel like home. She has her spells of being moody and vibey and spiritual, but her words are so easy to relate to.”

Spears lumping “Holiday” in with “Live to Tell” is fascinating. The former is a simple bubblegum pop song whose main appeal is its groove. It’s lyrics are so simple that a small child could understand them. Meanwhile, “Live to Tell” is an oblique, dramatic ballad that shows off the singer’s more mature side. 

Britney Spears worked with the Queen of Pop multiple times

Spears elaborated on her love for the Material Girl. “She’s a diva and does what she wants, but she’s a loving person. Madonna has done so much, and she’s been around so long, and the b**** still looks good,” Spears wrote. “She’s spent years in the public eye, and that can be really hard for anyone to deal with. But she dug deep and started writing from her heart.”

The connection between Spears and Madonna extends beyond the essay. The two pop stars worked together on the dance song “Me Against the Music” and kissed each other during a memorable MTV performance. Madonna also made an appearance in the documentary Britney: For the Record, where she compared Spears to herself. Spears also appeared onstage with Madonna to perform “Human Nature” while on tour.

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How Madonna’s ‘Holiday’ and ‘Live to Tell’ performed

While “Holiday” is often cited as one of Madonna’s best songs, it wasn’t one of her biggest songs. The tune peaked at No. 16 on the Billboard Hot 100, staying on the chart for 21 weeks. “Holiday” appeared on the album Madonna. That record reached No. 8 on the Billboard 200 and remained on the chart for 168 weeks — longer than any of the singer’s other albums.

“Live to Tell” performed better than “Holiday,” probably because it came out after Madonna became a megastar. It topped the Billboard Hot 100 for a week and stayed on the chart for 18 weeks in total. “Live to Tell” appeared on the album True Blue. That record reached No. 1 on the Billboard 200 for five of its 82 weeks on the chart.

“Holiday” and “Live to Tell” are two wildly different songs in Madonna’s discography but they have a similar effect on Spears.