As it has grown over the years, pop punk has become a major part of pop culture, even featuring music videos with significant celebrity appearances. Such appearances have been seen before, sometimes even music videos can define eras such as the MTV Generation.

Any time an artist can bring something extra memorable to their videos, it helps them achieve legendary status. When crossovers occur, they not only attract the fans of the musicians but also those of these particular celebrities. When these cameos succeed, they become revered and discussed by music critics, celebrating their iconic status. Now, with platforms like YouTube, it has also become easier to see which videos are watched repeatedly, signifying even greater importance.

8 Ashley Tisdale

Boys Like Girls - Love Drunk

In the mid-2000s, many bands rose to the forefront of pop punk, with Boys Like Girls being one of them. Within their first two albums, they released hit songs such as "The Great Escape," "Two Is Better Than One," and "Love Drunk." The latter features Ashley Tisdale, who makes a memorable appearance in the music video. At the time, Tisdale was a Disney Channel star, not only on television but also in film.

The music video is set in an arcade, and Tisdale plays the lead girl. Throughout it, she makes everyone fall in love with her until she makes a surprising choice at the end. The video provides some comic relief, but it perfectly depicts what the band was trying to convey. Even though Boys Like Girls became one of the 2000s bands that disappeared from the spotlight after their 2012 album, they released a new record in 2023, and with songs like this, their legacy remains firmly intact.

7 Rachael Leigh Cook

New Found Glory - Dressed To Kill

Following the success of their debut album in 1999, New Found Glory returned the next year with their self-titled sophomore record. While this did feature a re-recording of their big debut song, "Hit or Miss," another track that stood out was "Dressed to Kill." The tune received its own music video, which starred Rachael Leigh Cook. By the time the video was recorded, Cook had already appeared in well-known movies such as the Baby-Sitters Club and She's All That.

From the clothing to the story, it fits perfectly with the time period and now serves as a nostalgic reminder of the era.

With Cook's career on the rise, her inclusion in this video helped elevate the profile of New Found Glory, who were just starting to launch their career. The plot revealed the band performing the song in a garage. Cook portrayed the love interest, who was shown living her best life until she finally discovers who truly has a crush on her. From the clothing to the story, it fits perfectly with the time period and now serves as a nostalgic reminder of the era.

6 Will Sasso

Sum 41 - Still Waiting

With hit songs such as "Fat Lip" and "In Too Deep," the debut album of Sum 41 launched the band's career to a tremendous start. This generated excitement about what they would release next, and, as expected, they had more successful songs on the way. "Still Waiting" became one of the most memorable tracks on their sophomore record. Its music video helped it stand out among the slew of great tunes the band already had.

Getting the opening scene right for anything on film is crucial, as the goal is to hook the audience. Sum 41 achieved this, as the "Still Waiting" music video shows them meeting with Will Sasso, who plays a record producer. At the time, Sasso was gaining recognition for his roles in the shows Madison and Mad TV. His role in Sum 41's video benefited him just as much, as he had very memorable lines while trying to come up with a name for the band.

5 Chris Kirkpatrick & Kyle Gass & Mike Watt

Good Charlotte - Lifestyle Of The Rich And The Famous

After releasing a successful debut album, Good Charlotte returned with their sophomore record, ready to unveil more hits. Among these would be "The Anthem," "Girls & Boys," and "Lifestyle of the Rich & Famous." The latter featured a memorable music video that became a hit on MTV. The video shows the band performing the song, but along the way, they end up incarcerated. As these situations unfold, they eventually find themselves in the courtroom, where all these appearances take place.

Having them appear in different roles helped keep viewers engaged, as you had to watch until the end.

For each appearance in this video, the three different musicians play critical roles. Kyle Gass, known for his time in Tenacious D and various film projects, plays the prosecutor. Chris Kirkpatrick, known from *NSYNC and numerous guest appearances, plays the witness. Finally, Mike Watt from Minutemen plays the foreman. Having them appear in different roles helped keep viewers engaged, as you had to watch until the end, never knowing who would pop up next.

4 Ryan Reynolds & Tara Reid

Sugarcult - Bouncing Off The Walls

With their debut album, Start Static, arriving in 2001, Sugarcult received a huge boost when their hit single "Bouncing Off the Walls" ended up on the soundtrack for the movie, National Lampoon's Van Wilder. Not only did National Lampoon have a large following, but comedy movies like this were major players in cinema at the time. Helping add to the legacy was the fact that the film starred Tara Reid and Ryan Reynolds.

By the time the movie arrived in 2002, Reid had made a name for herself, appearing in many films of this nature. As for Reynolds, he had already appeared in several film and television projects, but his name has only grown since then. The music video featured scenes from the movie, which instantly made it recognizable. Although Sugarcult would go through ups and downs as a band following this, their relationship with the film has kept them in Hollywood's allure.

3 Jason Biggs & Mena Suvari

Wheatus - Teenage Dirtbag

Having already starred in the hit coming-of-age movie American Pie in 1999, Jason Biggs and Mena Suvari brought a ton of credibility when they appeared together in 2000's Loser. Helping to further build a following for the film, the two co-stars would once again share the screen, this time in the music video for the song "Teenage Dirtbag" by Wheatus. The plot would follow exactly how the lyrics of the song depict.

The 4x platinum-selling song has become a timeless classic and is still occasionally used to evoke nostalgia.

As the band performs, the two eventually fall in love, leading to a happy ending, but there is a twist. The dream ending is just that-a dream. With both of them in the song, this video became instantly recognizable for fans of the teen comedy stars. Their performances earned a nomination for Best Video at the Kerrang! Awards. Over the years, the 4x platinum-selling song has become a timeless classic and is still occasionally used to evoke nostalgia.

2 Kim Kardashian

Fall Out Boy - Thnks fr th Mmrs

In 2007, two major entities collided when Fall Out Boy secured Kim Kardashian's appearance in the music video for their song, "Thnks fr th Mmrs." The band had been on a meteoric rise since their huge sophomore record, From Under the Cork Tree, so in hopes of maintaining their momentum, they sought to tap into all relevant pop culture avenues. During this time, Kardashian's career was also on the rise as she became a prominent personality in the mainstream.

The video depicts the band attempting to have their video directed by a chimpanzee. Naturally, this becomes quite chaotic as things don't go as planned. Ultimately, Kardashian plays a key role as she shares a kiss with guitarist Pete Wentz. She then watches the end of the song with the director, before Wentz loses his cool, smashing lights and his guitar.

1 Alyssa Milano

Blink-182 - Josie

Before Blink-182 were singing about all the small things, welcoming Travis Barker as their drummer, and ascending to megastardom, they were laying the foundation for their success. Their second studio album, Dude Ranch, became the springboard for everything they wanted to accomplish. "Josie" was one of the special songs that helped permanently change their lives.

The music video for it has gone down as an interesting part of the band's history. Not only does it feature original drummer Scott Raynor, but it also includes Alyssa Milano. Up to this point, Milano was just building her career, having had a great start on Who's the Boss?. Following this, she would become one of the top actresses, and Blink-182 would become one of the top pop-punk bands. Therefore, this collaboration has now become legendary, and the significance of it cannot be understated.