Taylor Swift was one of the big winners at the 2023 MTV Video Music Awards on Tuesday, scooping up the trophy for best video for “Anti-Hero,” as well as best pop video, song of the year, and best direction.

The singer was presented the award for best pop video by boy band NSYNC, who reunited on stage especially for the VMAs. Swift was noticeably starstruck by seeing the group, which includes Justin Timberlake, back together.

She said: “I’m not doing well pivoting from this to this… I had your dolls! Like, are you doing something? What’s gonna happen now? They’re gonna do something and I need to know what it is! You guys, you’re pop personified, so to receive this from your golden pop hands, it’s too much. Thank you for the friendship bracelets.”

But this isn’t the first time that Swift and Timberlake have been supportive of each other. Here is what they’ve said about each other in the past.

Ellen DeGeneres surprised Taylor Swift with an appearance from Justin Timberlake in 2008.

Justin Timberlake and Taylor Swift at the MTV Networks Upfront at the Nokia Theater on May 8, 2008, in New York City. Bryan Bedder/Getty Images for MTV Networks)
Back in 2008, Swift went on “The Ellen DeGeneres Show” and host Ellen DeGeneres mentioned that the last time Swift was on the show, she had revealed her “musical crush” — Justin Timberlake.

In true Ellen style, the host then brought Timberlake out to surprise Swift.

The starstruck “Midnights” singer told Timberlake: “Wow! It’s really good to meet you. This is the best surprise ever. This is the best day ever.”

DeGeneres also asked Timberlake to share some dating advice with Swift, asking him why men are such jerks.

“Where do I start?” Timberlake responded. “Ladies, you are just smarter than us. See, I’ve accepted that. I’m much more comfortable in my stupidity and I just roll with it, you know? So that makes me less of a jerk.”

Timberlake interviewed Swift about shopping at Walmart in 2012.

Taylor Swift and Justin Timberlake at the Walmart shareholders meeting in 2012. YouTube
In 2012, Walmart celebrated its 50th year anniversary at its shareholder meeting, and to mark the occasion, Timberlake interviewed Swift in front of the audience about shopping at the store.

Swift introduced herself by saying: “My name is Taylor. I’m from Nashville. I’m a singer.”

Timberlake joked: “Of course you are. A singer? Whatever.”

Timberlake then asked Swift what she likes about Walmart, to which she replied: “I really like Walmart because my band and I like to go there. We go in there and they have everything we need. They have candy. And steaks. ‘Law & Order’ DVDs. Cat toys. Everything.”

It was bizarre, but hey, it made the headlines.

Swift brought Timberlake out to perform “Mirrors” with her on her 1989 World Tour in 2015.

Justin Timberlake and Taylor Swift on stage at the Staples Center in Los Angeles in 2014. YouTube
When Swift was touring her “1989” album, she brought Timberlake out at the Staples Center in Los Angeles to perform a song together.

“Okay, so I’m obsessed with his music. You’re obsessed with his music. There’s no one who’s not. It’s like the one thing in the world that everyone has in common,” said Swift as she introduced Timberlake.

She added: “He’s been a great friend to me, and he will be remembered as one of the greatest musicians of our generation. I can’t quite believe I’m about to say this, but Justin Timberlake is here.”

The duo sang Timberlake’s song “Mirrors,” which he wrote for his wife, Jessica Biel.

Timberlake honored Swift at the 2016 iHeartRadio Music Awards.

Taylor Swift and Justin Timberlake at the iHeartRadio Music Awards on April 3, 2016 in Inglewood, California. Frazer Harrison/Getty Images for iHeartRadio/Turner
The 2023 VMAs was not the first time that Timberlake has presented his longtime friend with an award.

At the 2016 iHeartRadio Music Awards, Timberlake presented Swift the award for best tour, after selling over two million tickets on her Reputation Stadium Tour.

Per Entertainment Weekly, Timberlake spoke about how successful Swift had become, and how many awards she had already picked up in her career.

“Word on the street is she’s in the pole vault at the Olympics in Rio and she’s favored to win,” he said.

Timberlake had more praise for his friend, adding: “Taylor chooses to knock down walls and invite everyone to be on her #squad.”

After the show, Swift thanked the “Mirrors” singer in a now-deleted Instagram post, reported Entertainment Weekly at the time.

Swift captioned a photo of them together at the awards: “Hero status, friend status, all time fav status. @justintimberlake thank you for absolutely everything.”