This is not an anti-Taylor Swift thread. And we all know Taylor Swift and Madonna are two different and very unique artists. This is just a question... A very honest, brutally honest question. Has Taylor Swift surpassed Madonna all-around?
1. In terms of social and pop culture impact. First, it was Paula Abdul; she started outselling Madonna in the United States. And for a brief period, Britney Spears seemed to be on her way to supplant Madonna... Until the kiss. And then it was Lady Gaga. And not so long afterwards, Taylor Swift ended up outselling and surpassing Lady Gaga. According to Elton John, Taylor Swift is a great songwriter, great artist, the biggest phenomenon since The Beatles. (And you know he'd never say that about Madonna! He even threw a fit when Madonna beat him for best songwriter at the Golden Globes.)
2. In terms of peak longevity... It seems like Taylor Swift's peak just never ends! From that 2009 VMAs moment (essentially her consecration and initiation) during which Kanye West interrupted her to her many wins last night at the 2024 VMAs, some would argue that her peak is outlasting Madonna's (though Madonna has had many peaks and highlights during her career).
3. In terms of artistry, mainly songwriting. Madonna is the author and producer (usually executive producer and co-song producer) of the vast majority of her catalogue. Madonna is also oftentimes the vocal melodist and/or co-composer. Madonna has some sole songwriting credits, and she plays the guitar. Taylor Swift and Madonna seem equal on those fronts, but many are under the impression Taylor Swift is more of a songwriter (a singer-songwriter as opposed to a singer and songwriter) and more of a guitarist. Heck, Taylor Swift was recently voted the eighth best guitarist of the last two decades!
4. In terms of youth appeal. Taylor Swift is now 34 years old and still appeals a lot to youngsters. At age 34, Madonna was singing "Erotica," "Deeper and Deeper," "Fever," "Bad Girl" & "Rain" and was perhaps seen as more adult contemporary. And as soon as she hit 35 and went on her Girlie Show Tour, some media already started calling her "old" and "grandma."
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Note: I must admit that the fame of Taylor Swift, esp. in this digital era, is unprecedented! I sometimes read that the era of big legendary megastars is over, but this doesn't seem to be the case of Taylor Swift.