Estelle vs. Olly Alexander | Head 2 Head

In the 3^rd edition of Head 2 Head (2024), Estelle and Olly Alexander (Years & Years) contend for the best rendition of “American Boy.”

Welcome to Head 2 Head! On Head 2 Head, we pit at least two musicians performing the same song, comparing their respective performances.  Then, after much deliberation, we deliver a verdict of which performance was the best, or at least, subjectively, which performance moved us more.  In the 3^rd  edition of Head 2 Head (2024), Estelle and Olly Alexander contend for the best rendition of “American Boy”. So, without further ado, let the Head 2 Head commence!

1. Estelle, “American Boy” (Ft. Kanye West)

💿 Shine • 🏷 Woah Dad! • 📅 2008

“I really want to come kick it with you / You’ll be my American boy.” Ah, those American 🇺🇸 boys are the best 😍! As talented as she is, unfortunately and unfairly, Grammy-winning British R&B artist Estelle (Estelle Swaray) has one big hit to her name stateside: “American Boy”. The 2008, multiplatinum, top-10 hit (peaked at no. 9 on the Billboard Hot 100) was produced by will.i.am. The backdrop features a sickening groove and exuberant synths. Assisting Swaray is the one-and-only Kanye West, long before he became far too controversial. That sole Grammy win came because of “American Boy,” which she penned alongside West, will.i.am, Caleb Speir, John Legend, Josh Lopez, Kanye West, Keith Harris, and Kweli Washington.  That’s lots of cooks in the kitchen, but, take one listen to this infectious gem from Swaray’s album, Shine, and you realize this is nothing short of an electrifying bop.  

Mr. West appears on the intro, gassing up the British musician for her big moment.  “This is a number one champion sound / Yeah, Estelle, we ‘bout to get down,” he asserts, adding, “Who the hottest in the world right now? / Just touched down in London town.” He’s not lying – he was hot stuff in 2008.  Moving on, what’s the premise? Estelle is all-in on boys stateside – The United States. Can you blame her 🤭? “Like the way he’s speakin’, his confidence is peakin’ / Don’t like his baggy jeans, but I might like what’s underneath them.” Damn! You could say she wants a ‘foreign,’ as the rappers might put it.  Ultimately, “American Boy” is an energetic, fun cut with a great beat – infectious to the nth degree.  Estelle sings beautifully, will.i.am drops the perfect backdrop, and West avoids being an asshole 😏, providing a nice lift.  Well, Mr. West is still cocky and confident as hell: “Who’s killin’ them in the UK? / Everybody gonna say, ‘You, K’” and “I’m feelin’ like Mike at his baddest / Like The Pips at their gladdest / And I know they love it / So to hell with all that rubbish.” Woo! “American Boy” remains lit at it approaches two decades in age.

Appears in 🔻:

• 50 Awesome Boy or Girl Songs (2021)
• Estelle, American Boy: 1 Hit WONDERful 2 (2024)

2. Olly Alexander (Years & Years), “American Boy”

🎵 “American Boy” • 🏷 Polydor / Universal Music Operations Limited • 🗓 2022

“Take me on a trip I’d love to go someday / Take me to New York, I’d love to see LA,” Olly Alexander, the sole member of Years & Years, sings.  He continues, “I really want to, come kick it with you / You’ll be my American boy.” “American Boy” in the hands of Alexander works seamlessly for many reasons.  One, is, he happens to be from England, just like the song’s original performer, Estelle.  Like Estelle, he wants in on the American boy train! Furthermore, it’s no secret Olly is gay, so, he eats up this Grammy-winning record original recorded by the opposite sex and makes it a fab addition to the LGBTQ+ collection. MNEK produces this sick cover.

“He said, ‘Hey, mister, really, really nice to meet ya’ / I just met this five-foot-seven guy who’s just my type.” A short king 🤴 – right on, Olly! In the hands of Alexander, “American Boy” is no copycat cover.  First and foremost, Olly and Estelle possess two completely different voices.  Furthermore, in this Years & Years take, the key is changed – C/ C minor versus E / E minor.  As far as his tone, Olly slays, wowing with his exuberant, light tenor.  The production is also updated for the 2020s.  Not that the original is dated or stale, but this more recent interpretation gets more of the synthpop treatment we’ve come to associate with the ‘collective.’ One of many selling points besides the rhythmic, slick instrumental are the smooth, harmonized background vocals – sweet, sweet, sweet! Estelle made “American Boy” a hit – one of the gems of the 2010s.  Olly Alexander does a magnificent job of reintroducing it to a new audience in the 2020s, PERIOD.

Appears in 🔻:

• Olly Alexander (Years & Years), American Boy: Covers No. 1 (2024)

The Verdict 👨🏿‍⚖️ 

Ah, here comes the moment of truth! Does “American Boy” belong to the originator, Estelle, or to the fresh, talented coverer, Olly Alexander? My boy Olly does a fabulous job of bringing “American Boy” to a new generation – updating its sound. Furthermore, he gives a gay perspective and we totally #STAN. That said, Estelle won a Grammy for the original, peaked in the top 10 of the pop charts, and earned a multiplatinum single.  So, the edge goes to the original, courtesy of the lovely, underrated Estelle Swaray.

Estelle vs. Olly Alexander: Head 2 Head No. 3 (2024) [📷: Brent Faulkner / The Musical Hype; Polydor, Universal Music Operations Limited; Hernán Toro, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]