The Britney Spears Music Video You Didn't Know Kevin Federline Was In

It goes without saying that Britney Spears' videography is every bit as brilliant as her discography. The Princess of Pop blessed us with dozens of bops over the course of her decades-long career. Hits like "...Baby One More Time" and "Oops!...(I Did It Again)" turned the then-teen into a household name when she debuted on the scene. Even a casual fan would likely be able to sing along to either track, and it's a safe bet they'd recognize elements of the music videos, too.

Boasting iconic looks like a schoolgirl uniform or red catsuit (via The Hollywood Reporter), awe-inspiring dance breaks (via Us Weekly), and the occasional controversial plot twist, every video in her collection is a testament to Spears' star power. They're critically acclaimed, too. Spears was awarded the Michael Jackson Video Vanguard Award at the 2011 MTV Video Music Awards (via MTV); that makes her one of an elite group including the likes of Madonna, Beyoncé, Jennifer Lopez, and Pink (via PopSugar).

Over the course of her career, "Toxic" hitmaker has shared screen-time with famous faces such as Madonna and Tinashe. On occasion, she also used her visuals as an opportunity to introduce fans to real-life romantic partners. For example, her then-boyfriend Jason Trawick appeared as a kind-hearted bad boy in her "Criminal" video in 2011 (via MTV). Even ex-husband Kevin Federline got a chance to shine. We're willing to bet you don't know which video he appeared in, though.

Britney Spears' relationship with Kevin Federline captivated the media. The diva fell for the former backup dancer after they met in 2004. They went public with their relationship (staging several sexy photo ops in the process) and were married by the end of the year. The newlyweds had two children — Sean Preston and Jayden James — before things imploded. Spears filed for divorce in 2006 and finalized in 2007 (via People).

It was a relatively quick run, but they immortalized their steamy romance on screen before it cooled off. In 2004 Federline made a cameo in the video for Spears' cover of Bobby Brown's "My Prerogative" (via YouTube). She reworked the rebellious anthem for a greatest hits record and pulled out all the stops in the accompanying visual. In it, the singer gate-crashes a party, which viewers later learn is in fact her own wedding. Of course, she says "I do" to Federline (while wearing an edgy black dress like a true rebel heart).

Her man makes a couple other quick appearances while Spears shows out in racy lingerie. Although both were renowned for their dance moves, neither pulled off a complicated routine for the project. Spears' mom Lynne Spears explained that was because pop star recently injured her knee and couldn't handle a high-intensity performance. Instead, the focus was on "capturing gorgeous close-ups and very subtle movement" (via MTV). It also captured a fleeting moment in pop history.

Let it be known the Princess of Pop is a generous soul. Britney Spears returned the favor of Kevin Federline's "My Prerogative" cameo by lending some star power to his then-budding rap career. The dancer dropped his only album "Playing With Fire" in 2006. The project was executive produced by Spears (via Showbiz Cheatsheet). She also sang on one of the tracks titled "Crazy."

While it cruelly isn't a reworking of her 1999 bop "(You Drive Me) Crazy," the song was one of Spears' only releases in 2006. That was enough for her music-hungry fans. On it, she sings about her indescribable relationship with Federline and hits back at critics. ""They say / I'm crazy / for loving you / for feeling you," she coos over club-ready beats. "Maybe/ I'm a little crazy / but they don't know / all the things you do" (via YouTube).

"Playing With Fire" was Federline's only album for a reason; it was critically panned. The project got an impressively low score of 15 on Metacritic. The summary on the site is... cutting to say the least. "Now that Britney has dumped him, all he has is his music. Ouch." There's a bright note, though. "Crazy" was lauded as the top track. Additionally, AllMusic dubbed Spears' hook "the only memorable piece of music on the record." At least she got the project some love?

Clearly Britney Spears and Kevin Federline's love was not made to last. The same could be said for the star's relationship with Jason Trawick. They called off their engagement in 2013 (via US Weekly). However, you could say that she had much better luck on the set of her "Slumber Party" music video in 2016. That's where Spears met her fiancé Sam Asghari.

In the video, the fitness model turned actor plays against Spears as a romantic lead. They share an infamous scene together where the legendary diva crawls across a table and licks up a puddle of milk from in front of her co-star (via YouTube). We wonder if the pair knew then what that fateful moment would lead to?

In a 2019 interview with Entertainment Tonight, Asghari revealed that he had previously starred in Fifth Harmony's "Work From Home" video. He also shared how he landed the gig of his lifetime. Apparently, a friend was working on the video and sent Spears' team his photo as a potential romantic lead. Clearly, Spears agreed with the casting decision. A couple months later, they met for sushi. The rest has been documented on Instagram over the years, and we certainly love to see it!