Strip Tees is a recurring series in which I write
about t-shirts I like
Beliebe it or not, you’re looking at perhaps the most historically significant t-shirt in modern pop music history.
The Date: December 11th, 2009
The Event: Z100’s Jingle Ball at Madison Square Garden in New York City
The Players: Taylor Swift, Justin Bieber, John Mayer, Jordin Sparks, Pitbull, Kesha, Jay Sean, Orianthi, Kris Allen, Owl City
I’m already hooked on the fact that it’s a bootleg. Bootleg or “unauthorized” concert tees have been around as long as rock concerts, and in fact it was concerts that helped popularize the wearing of graphic t-shirts in the first place. The rise of the “rap tee” in the 80s and 90s (read the book for a full history) cemented the bootleg aesthetic as a subcultural fashion force, and it’s from that tradition this Jingle Ball boot was born, featuring multiple artists arranged in an elegantly crafted, double-sided, sepia-toned composite (Tay Tay front and center, and for good reason as we shall explore).
For multi-artist concerts in particular, the “parking lot” tees are usually far superior to the official merch on offer inside the venue, which can’t encompass likenesses of the singers and bands fans came to see due to prohibitive licensing issues. Cases in point:






I’m also hooked on the throwback vibes conjured by this particular radio station and this particular concert event. As a 90s kid in the New York Tri-State with the Boomerest parents imaginable, turning the dial away from CBSFM 101.1 (“New York’s Oldies Station”) to 100.3 (“New York’s #1 Hit Music Station”) was the ultimate act of angsty pre-pubescent defiance. I made sure the family car was locked into Elvis and Elliott and the Z Morning Zoo on the way to school and Paul “Cubby” Bryant on the way home. Granted, my pop phase was relatively short-lived, curtailed by discoveries of hip-hop and classic rock that soon adjusted my frequencies down the dial to Hot 97.1 and up to Q104.3, but those formative years of Z100 zealotry and the relentless on-air promos and ticket giveaway enticements to which I was subjected created an almighty aura around their signature end-of-year extravaganza: Jingle Ball (presented by H&M / Aeropostale / Goldfish Puffs / Capital One).
Would a Jingle Ball tee from ‘96 or ‘97 more accurately reflect my personal nostalgia? Sure, but with all due respect to Shawn Colvin, Melissa Etheridge, Savage Garden, and Chumbawamba, those early rosters can’t hold a candle (in the wind) to the everlasting pop-cultural lore we find in the ‘09 jamboree and its commemorative tee.
2009 as was a banner year in general. It began with the United States of America inaugurating its first Black President, 220 years after the election of its first president — who, like nine of the first eleven presidents, owned slaves!!!). The first Bitcoin software was publicly introduced, and thus the first Crypto Bro was created (Hal Finney, who purchased 10 coins from creator Satoshi Nakamoto — what would have been a fantastic investment had he not died in 2014). The first episode of Modern Family aired, inspiring the first of many Sofia Vergara-inspired boners. Michael Jackson truly “beat it” (it being this physical plane of existence), but the new King and Queen of Pop were in the midst of being crowned..
As 2008 became 2009, Taylor Swift appeared live from Times Square as the first musical guest of Dick Clark’s New Year’s Rockin’ Eve, introduced by Ryan Seacrest as “a great artist and impressive songwriter as well,” performing a medley of four songs from her Diamond-certified second album Fearless that had released in November. It spent 11 weeks atop the Billboard 200 charts and laid the foundation for 2009 to become The Year of Living Swiftily. It was the year she firmly crossed over from her country music roots, taking her from playing Strawberry Festivals and Frontier Days to headlining a sold-out Madison Square Garden and Staples Center, among dozens of other Stadiums, Arenas, Coliseums, Pavilions, even a Palace (of Auburn Hills). Each show sold out within 60 seconds of going on sale, and when the tour finally wrapped after six countries and 118 dates, the 20-year-old was $66 million richer.
It’s hard to imagine a bigger breakout than Taylor Swift’s in 2008-09, but hot on her heels was another, even younger pop megastar in waiting. Almost a year to the day of Taylor’s Fearless release, a 15 year-old bowl-cut Canadian named Justin Bieber dropped his debut EP My World. Of the seven tracks on the record, four would become Top 40 hits, and the album would eventually be certified 3x platinum as Biebermania took hold over the winter of 2009-10 (like Swift’s the year before, Bieber’s appearance on Dick Clark’s New Year’s Rockin’ Eve signaled his arrival on the international pop music and exotic monkey ownership scenes he would soon come to dominate).
So here we are on December 11th, 2009, at the World’s Most Famous Arena, where the world’s two most famous teenagers are sharing the stage at Z100’s iconic holiday concert. But wait - there’s more! John Mayer, who at this point was enjoying his seventh year as one of the most critically acclaimed/culturally adored pop rock singer-songwriters on the planet with seven Grammy wins and three multi-platinum studio albums to his name — soon to be four with Battle Studies having released on the same day as Bieber’s debut (November 17th). Mayer had become an unabashed Taylor fan over the past year and invited her to collab on what became the third track on his new album, “Half of My Heart,” which they played live together for the first (and only) time on this auspicious night at MSG.
Subsequent sightings together in Nashville and retroactive timeline detective work around Swift’s previous relationship with Taylor Lautner led many to believe that it was after this Jingle Ball concert that Mayer stuck his 32 year-old cock inside Swift’s 19 year-old snatch for their premier pump sesh.
KESHA IS ALSO ON THIS SHIRT. The lead single “Tik Tok” from her debut album Animal was released on August 7, 2009, and by the time Jingle Ball rolled around it had reached No. 3 on the charts (would be No. 1 by New Year’s Day). KESHA RULES. And talk about a prescient song title…
As if all this wasn’t enough, allow me to continue painting the picture of pop prestige represented on this single tee. It’s hard to name a more culturally, historically, AND aesthetically significant television show in the history of the medium than American Idol. Despite signs by 2009 that the series had plateaued in popularity, Idol was still the country’s number-one rated primetime program with 25 million average viewers for its Season 8 that saw Kris Allen edge out Adam Lambert for the microphone-shaped trophy after nearly 100 million votes cast during the finale (a new world record for a televised singing competition).
Allen and Lambert were both on the Jingle Ball bill and earned placement on the shirt (Lambert — the much bigger star 15 years on — in name only), but it’s another Idol winner facing front with premium position: Jordin Sparks, whose second studio album Battlefield had been released over the summer and helped her make history as the only American Idol contestant to have their first five singles peak within the top 20 of the Billboard Hot 100 chart. I can’t say I know a single one of those songs, but good for her! She seems nice.
Despite being a charttopper in his native UK, Jay Sean was introduced to American audiences in 2009, when his single "Down" (featuring Lil Wayne) topped the Billboard Hot 100 in October, making him the first solo artist of South Asian origin and first UK urban act to reach No. 1. Niche musical history, but HISTORY nonetheless!
PITBULL IS ON THIS SHIRT. Mr. 305 had already made a name for himself, mostly for repeatedly shouting “CULO!” alongside Lil Jon. But 2009 is the year he truly went WORLDWIDE with Pitbull Starring in Rebelution, released on August 28, and the two massive hits it spawned in “I Know You Want Me (Calle Ocho)” and “Hotel Room Service.” Pitbull is supremely stupid, but you can’t deny the impact he’s had on Carnival cruises and guys who ride their bikes shirtless up and down South Beach blasting music from bluetooth speakers. Also, CULO!
I had no idea who or what Owl City was when I first saw the name, but then Google told me he’s the guy who wrote this banger:
I always assumed this was by Postal Service or Death Cab or some other Ben Gibbard spin-off/side project. But no, Owl City is an entirely separate person named Adam Young who, as it turns out, has been critically shit on for appropriating the Gibbard vibe. Nevertheless, I fuck with “Fireflies,” and I find it hilarious that he’s on this shirt.
Finally, there’s Orianthi. Who? Well, if you’re Australian you’d know her. Her major label debut came out in October 2009, which produced the iTunes Single of the Week “According to You.” She’s widely hailed as one of the top female guitarists in the world, and boasts collaborations with many an aging axe-wielder, but she’s perhaps most famous for what never happened, as she had been handpicked by Michael Jackson to be his lead guitarist in his planned comeback residency at the O2 Arena, This Is It. The concerts were never to be, as MJ was found dead eighteen days before the first slated performance, but Orianthi played and sang at his globally televised memorial service and appears in the This Is It film documenting the show’s rehearsals. HISTORY? YES! MORE HISTORY!
Taylor. Bieber. Mayer. Kesha. Pitbull. American Idols. South Asian representation. Postal Service derivation. Do you get it now? Do you see what I see? Do you understand why I’ve listed this shirt for sale at QuizDaddys.com for $195, before tax and shipping? And that’s a STEAL if you ask me, considering its value will certainly rise once the Smithsonian adds it to its archives. Tag a Swifty, and stay tuned for more stories behind the shirts.