From Lena Dunham to Pitbull: Taylor Swift’s Wonderfully Weird 1989 Tour Guests

To honor Taylor Swift’s latest rerecording, we’re celebrating 1989 (Taylor’s Version) Week at The Daily Beast’s Obsessed. That means we’re throwing it back to 2014, to re-live everything that Taylor—and the rest of pop culture—was up to.

For me, Taylor Swift’s 1989 era had two major takeaways: One: Swift was capable of making an iconic, purely pop album. And two: She had a seemingly endless rolodex of celebrity friends.

In 2014, there was hardly an outing where Swift wasn’t photographed with a Victoria’s Secret Angel or fellow, usually less-popular musician by her side. Thus, the infamous “squad” was born. She even capped off the year with a star-studded 25th birthday party, which included guests like Justin Timberlake, the Haim sisters, Sam Smith, and, most shockingly, Beyoncé and Jay-Z, who couldn’t be bothered to attend Kimye’s wedding some months prior.

Then there was Swift’s mammoth 1989 World Tour the following year, where she really flexed her industry connections. Each night of the U.S. leg featured an illustrious—to varying degrees—guest. Swift claimed she wanted to add an element of surprise to a show that fans were otherwise bound to spoil on social media. “They know the set list,” she said in a Beats 1 interview following the tour. “They know the costumes. They’ve looked it up. That presented me with an interesting issue.”

The Defining Figures of Taylor Swift’s ‘1989’ Era1989 (TAYLOR’S VERSION) WEEK

Fletcher Peters, Allegra Frank

And boy, did she go through everyone in her contact list to solve it. Some of the tour’s guests of honor were models. Some were athletes. Some were Swift’s favorite television detectives. Some were random artists occupying the Billboard Hot 100. Some were Chris Rock. And Swift, who gave each of her guests an overly sentimental introduction, claimed to admire them all.

Given how active I was on Tumblr at the time, I’d like to think that my memory of this tour is quite fresh. I can specifically recall the hullabaloo over Swift’s MetLife show, where she invited Martha Hunt, Lily Aldridge, Hailee Steinfeld, Gigi Hadid, and Lena Dunham on stage during her performance of “Bad Blood.” It bears mentioning that Dunham, not a six-foot-tall stick-thin model (and a target for her average-sized figure at the time), stuck out in the photo and went on to say she felt “chubby” alongside the rest of the women. The oddness also stemmed from the sight gag of the creator of Girls looking like she had just left a meeting at HBO’s headquarters strutting onstage at a major pop concert.

Taylor Swift Was Once the Queen of Victoria’s Secret1989 (TAYLOR’S VERSION) WEEK

Helen Holmes, Allegra Frank

But Dunham’s cameo was hardly as bizarre as things got on this wild tour. Looking back at the random assortment of celebrities who graced Swift’s stage, either to sing a duet or simply strut down the runway, is a bit staggering. What was Matt LeBlanc doing at a Swift show? Did anyone in the audience know who Joan Baez was? What made Taylor think of Avril Lavigne in the year 2015? (Same with Leona Lewis.) Remember Andy Grammer?!

Other unlikely guests—although some of them were appropriate for the city she was visiting—included Mary J. Blige, Ricky Martin, Alison Krauss, Nelly, Wiz Khalifa, Mick Jagger, Kobe Bryant, Dwyane Wade, Lisa Kudrow as Phoebe Buffay, and Uzo Aduba, thankfully not as Crazy Eyes.

In terms of musical guests, though, Swift really captured the zeitgeist before Spotify defeated FM radio and fractured everyone’s musical tastes. She invited numerous smaller artists who were responsible for the past year’s biggest hits, including Nico & Vinz, OMI, MKTO, Rachel Platten, Sydney Sierota from Echosmith, Alessia Cara, and Walk the Moon. She also brought out Idina Menzel, dressed as Elsa, to perform the biggest song in the world at the time, “Let It Go,” from Frozen. Swift, who’s always down to clown, was predictably dressed as Olaf.

This particular list of pop acts—many of them certifiable one-hit wonders now—reads like a historical record representing the last gasp of monoculture. (Remember when we all knew the same corny songs before “prestige” pop took over?) It also marked Swift’s rise from a country ingenue to a high-profile, mainstream musician with enough credibility to cosign other artists—even if her seal of approval didn’t really keep them around that long.

In 2023, Swift doesn’t need any additional star power on her tours to get publicity. Her loyal Swifties have spent the past year clogging up our social media feeds with Eras Tour footage. And all of the celebrities attending her concerts thus far—minus Ice Spice—have been corralled under a tent or rocking out in their own suites. Plus, the opening acts on her Eras Tour are a more curated group of friends and respected musicians, including HAIM, Phoebe Bridgers, and Paramore. Regardless, Swfities will never forget all the PR efforts she made to get to this point, including belting her heart out with Pitbull.