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  • Writer's pictureStand-Up Comedy Historian

Bo Burnham and Taylor Swift: A Timeline of Their Interactions

Updated: Feb 8

Hi, everyone!

It's been exactly one week since THE incident that has provided the most concrete evidence yet that Bo and Phoebe Bridgers are definitely dating.

And where did that kiss seen 'round the world occur? Why at a Taylor Swift concert, of course!

But the funniest thing about all of the hubbub over Phoebo is that this has oddly coincided with Taylor dating Matty Healy, the lead singer of The 1975.

And, boy, is this group incestuous or what? It seems like everything Taylor does can be easily linked to Phoebe or Bo nowadays, including their friendships with people like the Bleachers' Jack Antonoff.

Bo and Phoebe even had that weird throuple kiss with Matty in December last year!

Anyway, because of all the recent news with Taylor Swift, Phoebe, Bo, and their friends, I wanted to compile a list of Bo's weird interactions with Taylor over the years. From calling out her similar-sounding songs and her championing of meritocracy on Conan to being on the same record label and attending her Grammys afterparty in February, Bo has had a real love-hate relationship with one of the biggest pop stars in the world over the past 17 years.

Let's dive in!

Bo's YouTube Years

Bo is one year younger than Taylor in age (yeah, he was born in 1990), and they both started becoming famous around the same time (2006). While Bo's popularity rose on YouTube with his somewhat-risqué comedy songs and clever wordplay, Taylor was putting out teen romance country pop. And Bo had a decidedly mixed reaction to her music.

Although he did know and like her songs, Bo would often complain about how they all sounded exactly the same. He mentions it during this interview for a radio station, and he plays two songs at around 4:05 in (Love Story and You Belong With Me) during this 2009 livestream that he says have IDENTICAL chords (an issue he later returns to in Repeat Stuff). He points out that his music sounds the same too, but at least he admits it.

And, in 2010, he wrote a Facebook post about Taylor and her somewhat insipid lyrics, pointing out that saying she wears "sneakers" is an easy way to ingratiate herself to her fans.

As you can see, Bo says he "loves Taylor" and that she's a "genius," but that did not mean that he was oblivious to how she often manipulates her audience, a theme that would continue into the 2010s.

what. and Vine

While he was promoting his second comedy special, what., in 2013, Bo was also making a name for himself as a popular Viner and tweeter. As such, Taylor Swift's name comes up again and again on these social media apps.

In terms of Twitter, Bo reached out to the Taylor Swift account about a Rolling Stone interview.

Bo also mentioned in a 2014 tweet that people often have weird expectations for Taylor.

And Bo even created a Vine about Taylor, pointing out how ridiculous her Diet Coke ad was where she is "writing" in her journal.

Make Happy

His next comedy special saw the return of Bo discussing Taylor and how she helps cultivate parasocial relationships with her fans.

First, there is the viral "advice" Bo gave during an interview with Conan O'Brien.

I would say don't...don't take advice from people like me who've gotten very lucky. You know we're very biased...Like Taylor Swift telling you to follow your dreams is like a lottery winner saying, "Liquidize your assets. Buy Powerball tickets—it works!"

And there is NO way to hear his diatribe in the middle of his Netflix special about how he doesn't love his fans and not think of Taylor and her Swifties.

Indeed, a fan caught Bo ranting about Taylor during one of his performances:

It's like Taylor Swift. She always soaks in. Every concert she lets everyone applaud. She stands there, and she's [Bo acts like he's basking in the appreciation of his audience]. It's like good, Taylor. You deserve 10 seconds where it's all about you. Can't it just be...can't it just be about Taylor Swift for once? Poor girl, picking up trash on the highway every day for 9 hours!

After he left live comedy to pursue screenwriting, directing, and acting—only to return in 2021 with his masterpiece—Bo apparently made a large impact on Taylor in his works and vice versa.

Inside and Folklore

An intrepid Redditor posted that Bo's aesthetic in White Woman's Instagram is quite similar to Taylor's in Folklore: The Long Pond Studio Sessions. I have to admit the similarity in appearance is uncanny, but I personally think the outfit Bo has on with his butt cheeks hanging out looks even closer to that style!

In addition, I found a 2021 Australian article about Taylor Swift and parasocial relationships (a topic Bo has harped on since 2013) that includes Bo's explanation of the phenomenon on the what. album:

There are literally so many deeply academic papers on the phenomenon of parasocial relationships in music, but for brevity’s sake let's turn to a 20-second exchange between a fan and comedian Bo Burnham from his 2013 comedy special what. for clarification.
Fan in audience: I love you!
Bo Burnham: You love me? That’s very nice. You love the idea of me, you don’t know me but that’s okay. That’s called a parasocial relationship, it goes one way and is ultimately destructive but please by all means keep buying all my shit forever.

Speaking of parasocial relationships, Swifties took it to another level with their recent open letter to her to stop dating Matty because he's too insane and presumptuous of them that they think they should control her love life!

Anyway, after Bo's polemic against fame and the overwhelming success of Inside, a certain silver-haired singer-songwriter entered the picture and changed everything.

Phoebe and That Funny Feeling

I'm not going to discuss all of this again (you can check out my full timeline on Phoebo's friendship here), but I did want to point out that Bo's growing closeness to Phoebe coincided with the softening of his stance against Taylor Swift.

As I've mentioned previously, Matty and Jack are also good friends with both, and I think this—along with Phoebe—has affected his perception of the pop star.

Or he's just playing nice because his new girlfriend is close to Taylor...who's to say?

Midnights and The 1975

According to Insider, Bo's brilliant special likely influenced Taylor and her songwriting on her recent album. The reasoning is that Taylor was absorbing Bo's criticisms of her persona and really tackling how she handles her fame and celebrity status. Plus, Jack Antonoff apparently co-wrote the majority of the songs and has produced all of Taylor's albums since 1989...and he's connected to Bo since they are friends.

Fun fact: Jack is also good buddies with comedian Mike Birbiglia who wrote a lovely tweet about Inside's Emmy nominations!

Anyway, the article presents a few possibilities as to how Bo and his works might have affected the album:

But may I present another potential influence: Bo Burnham. 
"Dear Reader" sounds like Swift was one of the many people who got really into Burnham's art after the release of "Inside" last year. It's as if she went down a rabbit hole, found the interview where he encourages fans not to "take advice from people like me who've gotten very lucky" (he explicitly includes Swift in that category), and then chased it with "Can't Handle This" from "Make Happy."
This isn't a huge stretch. We know from "Would've, Could've, Should've" that she's seen "Promising Young Woman" and the pair have a mutual friend in Phoebe Bridgers. But even if I'm way off base here, I'm still going to continue believing the vocal distortion is meant to emulate Burnham mocking Kanye West. I just know Swift would've gotten a real kick out of that. 

Midnights also features the song Maroon that many Bo fans think sounds surprisingly similar to All Eyes on Me. Someone even made a mashup of the two songs, and it looks like from the comments that others feel the same way!

In addition to putting out her own album in 2022, Taylor was listening to Matty's newest one—and so was Bo apparently.

Yes, it's true! Per Pitchfork last August, Being Funny in a Foreign Language was heard by Taylor and Bo prior to its release in October:

Taylor Swift, who got an early listen to the record, summed it up in three words: “It’s so funny.” Most of Healy’s friends are comics, and their approval of his work is particularly important to him: He played the album for musical comedian Bo Burnham, and was pleased when Burnham laughed at all the right times. Healy jokes he was furious when he heard Burnham’s 2021 song “That Funny Feeling,” which lists out society’s ills on the eve of destruction, a la “Love It If We Made It.” “He needs to stay in his lane a little bit,” he adds with a grin. “When he did that song, I was like, ‘You motherfucker.’”

Here's a video of Matty explaining how he sought the opinions of both to make sure there was enough humor mixed into the lyrics. He also calls Taylor "amazing" and says that there's a track they made together that's not seen the light of day...interesting!

The Grammys

If you'd have told me a year ago that Bo Burnham would attend Taylor Swift's Grammys shindig in February 2023, I would have told you, a year ago, interesting now leave me alone...

This was absolutely SHOCKING to the fandom because Bo has consistently stated how much he despises famous people and all the trappings of celebrity in Hollywood. For him to be at such a party was completely antithetical to everything we thought we knew about him (ah, he's proven himself right yet again!).

A fun fact about that night is that while he was taking pictures with Lana Del Rey's brother (who is seriously Bo's doppelgänger), Bo's recent ex-girlfriend, Lorene Scafaria, and his good friend Armen Weitzman were also in attendance. I'd love to know how they all interacted together!

The Eras Tour

And now we are back to the present day. Phoebe has been performing with Taylor on the Eras Tour, even having Matty playing with her when she opened in Nashville.

Then, of course, we had the kiss captured by Keith Urban in...where again, Bo?

Ah, that's right.

And Matty has been hanging out this spring with Bo and Jack as well as Bo's best friend Jerrod Carmichael (who had his picture taken with Phoebe at a pre-Met Gala party recently!).

Speaking of Jerrod, he knows Taylor as well!

During a Howard Stern interview last year to promote Rothaniel and On the Count of Three, Jerrod said that he actually uses this photo of him and Taylor Swift that was taken at Lena Dunham's wedding as his Grindr profile pic!

Another fascinating connection is Kate Berlant's eponymous one-woman play that Bo had directed (and I saw him in person there at 3 separate shows!).

Matty had attended a few performances apparently and even scored one of the KATE hats worn by the staff (they did not sell those as merch!).

We'll have to see what the future brings for all parties involved (and if Taylor and Bo will ever have a photo together!), but I hope you've enjoyed this deep dive into their odd interactions over the years.

Thanks for reading, and keep it here for more fun!

2024 Grammys Update: Oh yeah, they have been in a photo together!

And Taylor was photographed AGAIN with Jerrod at a football game recently—woot!


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