Madonna and Taylor Swift both kicked off their careers by releasing self-titled debuts. However the similarities end there. When the future Material Girl dropped her opening blush-inducing salvo in 1983, she was an ambitious 23-year-old, Downtown, New York chic, dance floor vixen ready to turn on and offend the world. By contrast, Swift was 15 and a wide-eyed country music neophyte barely done with her freshman classes. So why would Enstars even attempt to compare these two drastically different artists? Because Madonna and Swift have both ruled their respective eras as pop royalty. We break down their match-up through their first five studio albums. Who comes out on top? Read on!

Madonna (1983)
Taylor Swift (2006)
When Madonna was released in the summer of '83, Ms. Ciccone was initially embraced more by R&B radio as tracks like "Lucky Star," "Holiday" and "Everybody" displayed meatier, funkier grooves. It's on the saccharine "Borderline," Madge's first top 10 hit, that her future as the reigning Queen of Pop was given a knowing glimpse. Even back then her mission to push our buttons was clear: "Unlike the others I'd do anything/I'm not the same, I have no shame/I'm on fire," she announced on the lustful "Burning Up."

Swift embraced a more heartfelt, ain't-that-cute innocence: "When you think Tim McGraw, I hope think my favorite song..." she sung on her debut single which name checked the country music superstar. On the flip-side is "Picture to Burn," on which a scornful Swift snipes, "I realize you love yourself more than you could ever love me....I hate that stupid ol' pick up truck, you never let me drive..." To her credit, Swift avoids the usual teeny-bopper trappings, presenting herself as an earnest, intelligent spokesperson for the tween crowd. But really, this first match-up is a bit lopsided. The more seasoned Madonna was aiming for the kind of mammoth fame that would find her sitting at the same table as fellow '80s pop innovators Michael Jackson and Prince in two years time. Swift was just happy to sing her song.

Winner: Madonna

Like a Virgin (1984)
Fearless (2008)

Madonna straps on a wedding dress and becomes a music icon. Indeed, there is a reason Like a Virgin is viewed as the Detroit native's signature album despite the fact that it rarely hits the sophisticated, genre-pushing sweet spot of the pop provocateur's follow-up releases. Amongst its five singles, three have become Karaoke standards (the controversial MTV staple "Like A Virgin," the delightfully playful "Material Girl," and the swaggering "Into The Groove"). As populace statements go, Madonna's 10-million-selling set has overcome its, at times, over-the-top theatrics to become a landmark record that is the definitive template for the pop vixen (Britney Spears, Rihanna, and Katy Perry, we are looking at you).

Taylor Swift's follow-up finds the country sweetheart taking a decisive artistic leap as a songwriter without ever coming off as pretentious. The monster cuts ("Love Story" and "Your Belong To Me") are sneaky good. And when Swift speaks to the girls on "Fifteen," it's as if she is their best friend giving them advice on how to deal with that first kiss. Fearless has commercial cred (no. 1 on the Billboard 200; nearly 7 million copies sold in the States alone) and critical notice as even grizzled, jaded observers were impressed with Swift's surprisingly mature take on love lost: "Back then I swore I was going to marry him someday, but I realized some bigger dreams of mine..." Not bad. But Madonna's Like A Virgin carries a much more pivotal impact decades later.

Winner: Madonna


True Blue (1986)
Speak Now (2010)

True Blue is the sound of Madonna in love. Easily the most whimsical, optimistic work in her catalogue, even the serious minded numbers ("Papa Don't Preach" and "Live to Tell") have killer, sing-along choruses. The title track worships at the altar of girl-group pop perfection and the Spanish-inflected "La Isla Bonita" shows an evolving artist taking chances. A happy Madonna ("No more sadness, I kiss it goodbye") is an on-fire Madonna. But it's not all roses and lollipops on Swift's Speak Now.

Now 21, she is officially a grown woman and has gone through her share of toxic relationships. It is here her reputation as being the one ex-girlfriend you do not want to piss off is fully formed. Swift can be quite ruthless ("Better Than Revenge" goes nuclear on a cheating lover and his home wrecking conquest: "She's better known for the things that she does on a mattress!"). But just as noteworthy as her two-fisted lyricism is the production's more rock and pop leanings. Swift's turns down the country. Guitars are now a bit crunchier, meaner. And "Sparks Fly" exemplifies the album's bigger-is-better formula. It thumps.

Winner: Taylor Swift


Like a Prayer (1989)
Red (2012)

It's been called Madonna's most complete, serious artistic statement. Like a Prayer is a brave departure from the usual pure pop constraints. It, even (gasp!!!) challenges listeners to think beyond girl-meets-boy cliches. "Like a Prayer" turns her Catholic upbringing inside out equating spiritual redemption with sexual nirvana. "Spanish Eyes" takes on the devastating specter of AIDS and "Keep It Together" speaks on the importance of family unity. Don't get it twisted. Madonna still wants you to dance ("Express Yourself" dares you to stay seated). But Like a Prayer aims much higher.

On Red Swift officially becomes a superstar. But there's a lot more happening here. The opening of "State of Grace" sounds like it was taken from a session from U2's Joshua Tree. And while no one would ever confuse Swift's vocals for a young Reba McEntire, she still manages to challenge her understated VOX. "Treacherous" goes for the slow build-up and pays off with a undeniable hook while "22" flips to full-on pop, offering a preview of the more bombastic sounds of 1989.

Winner: Madonna

Erotica (1992)
1989 (2014)

Let's be clear. Erotica stumbles not because Madonna had the guts to celebrate her sexuality with unbridled empowerment. It stumbles because it's not much fun. Madonna's concept album unleashes her leather-and-whips alias Mistress Dita and goes for broke on the steamy title track ("There's a certain satisfaction in a little bit of pain..."). The heartbreaking "Bad Girl" is decent enough and "Bye Bye Baby" is easily the most upbeat offering here. But like its coffee table companion book Sex, Erotica is buried by its own self-indulgent weight.

Swift's 1989 may be anathema to country music purists, but it sure masters the art of the indelible pop record. How does she get away with it? By taking the easily-tossed genre very seriously. Sure, it's easy to roll your eyes at such stadium-ready numbers as "Welcome to New York." But soaring cuts like the eclectro-pop of "Blank Space" make up for the calculated fluff. The high speed "Shake It Off" still sounds like a triumphant curve pitch as Swift gets her boogie on and more synths jump out on "Out of the Woods," which may or may not be about her brief relationship with One Direction's reigning poster-boy Harry Styles. Whatever. If nothing else, the blockbuster that is1989 finds Swift at her complete world-beating powers.

Winner: Taylor Swift

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