Talk about a blast from the past, right? I mean, who would’ve thought that in 2024, one of the biggest headlines would involve Ryan Cabrera, Ashlee Simpson, and a whole lot of nostalgia. It just goes to show, you can take the pop culture out of the early 2000s, but you can’t take the early 2000s out of us. And honestly, I’m here for it. All of it. Especially when it involves a little stroll down memory lane with a couple of pop-punk sweethearts.
There’s something universally charming about exes who genuinely cheer each other on. No drama, no shade, just pure, unadulterated excitement. And that’s exactly what Ryan Cabrera is serving up regarding Ashlee Simpson’s return to music. You know, that whole Las Vegas residency thing? Yeah, that. It’s not just a comeback; it’s a moment. And Ryan, bless his heart, is practically leading the fan club, apparently even getting his wife in on the action. Talk about evolved. Or maybe just realizing some good music is good music, regardless of who made it.
It kind of makes you wonder, doesn’t it? Are we all just craving that specific vibe from twenty years ago? That raw, slightly angsty, totally relatable sound that defined a generation? Probably. Definitely. It feels like the universe is saying, “Hey, remember when things were… simpler?” And Ashlee’s music, in a lot of ways, was the soundtrack to that simpler, yet equally complicated, time.
“On the Way Down” and a Trip Down Memory Lane
So, here’s the thing- Ryan Cabrera is out there celebrating the 20th anniversary of his hit single, “On the Way Down.” Can you even believe it’s been two decades? I swear, it feels like yesterday I was blasting that song, probably right after watching an episode of The Ashlee Simpson Show. Which, coincidentally, was also the same year Ashlee starred in his music video. Full circle, much? It’s like the universe is having a little laugh, reminding us all of our questionable fashion choices and undeniable musical taste from back then.

A Collective “I Wanna See That Show!”
Ryan told Us Weekly, and I’m paraphrasing here, that everyone’s buzzing. “Everybody’s excited for that. I mean, all of my friends are hitting me up going, ‘Hey, I was gonna go to Vegas. Do you think we can go see Ashlee?’ I’m like, ‘Dude, I would love to see that show.’ Even my wife,” he shared. This isn’t just polite ex-speak; this is genuine excitement. And you know what? I get it. It taps into that specific vein of nostalgia that’s been running rampant lately- the Y2K aesthetic, the early 2000s revival, it’s all part of it.
- The Buzz: Ryan’s social circle, his wife, even he himself, are genuinely excited about Ashlee’s Vegas gigs. It’s not just a polite nod; it’s significant interest.
- The Draw: It seems like people are drawn to the idea of revisiting those specific albums. There’s a comfort in the familiar, especially now.
My favorite part? He even messaged Tina– Ashlee’s mom! That’s a deep cut right there. That implies a level of familiarity and respect that goes beyond typical celebrity pleasantries. It’s almost like saying, “Hey, remember old times? This is cool, right?” And yes, Ryan, it’s very cool. It’s a testament to the enduring impact of those early aughts artists, how they carved out their space and stayed there, even if quietly for a bit.
“I mesaged [her mom] Tina when I saw that was going on, and it made me say, ‘Oh my God, I want to revisit those albums.’”
Pop Culture Echoes and The Ashlee Simpson Show Legacy
Speaking of The Ashlee Simpson Show, let’s not pretend that wasn’t a cultural moment. It basically laid the groundwork for a lot of what we know as reality TV today- a younger celebrity navigating life, love, and a burgeoning music career. It was raw, it was a little messy, and it was undeniably captivating. The show, and Ashlee’s music, existed in a time when pop stars were still… accessible, in a way that feels a bit lost now. You truly felt like you were watching her grow up, song by song, episode by episode.
Beyond The Infamous Snaps
Okay, let’s address the elephant in the room. The famous SNL performance. We all remember it. It was a whole thing. But what often gets lost in that narrative is the genuine talent Ashlee had, and still has. Those albums- Autobiography and I Am Me– they hit different. They were anthems for a lot of us, capturing that specific teen angst with a pop-punk edge. They explored themes of self-discovery, heartbreak, and really, just figuring things out. And to hear Ryan Cabrera, someone who was right there in the thick of it with her, echoing the desire to “revisit those albums”-that’s powerful. It’s like he’s saying, “Don’t forget the good stuff.”
- Impact of the Show: It was more than a reality show; it was a candid look at an artist’s journey, making her incredibly relatable.
- Musical Merit: Beyond the drama, her early albums were genuinely a soundtrack for a generation, full of relatable lyrics and catchy hooks.

It’s interesting to consider how this kind of reunion, even if just in spirit with mutual appreciation, impacts both artists’ legacies. For Ryan, who’s celebrating twenty years of “On the Way Down,” it shines a spotlight on a past chapter that was formative. For Ashlee, it adds another layer to her comeback narrative, showing that even after all this time, the people who were there from the beginning are still rooting for her. It’s a nice story, you know? A really nice story in an industry that’s often anything but.
So, what does this all mean? Beyond the “aww” factor, I think it’s a sign that we’re all still hungry for genuine connection and authentic artistry. And sometimes, that comes from looking back, remembering the artists who shaped our younger years, and giving them the props they deserve. Because let’s be real, a good song is forever. And a good ex who remembers that? Even better. It just makes you wonder, who else from that era is going to surprise us with a comeback that everyone, even their famous exes, is excited about?
Maybe it’s a testament to good vibes conquering all, or maybe it’s just that good music, even two decades later, still scratches an itch. Either way, if Ryan Cabrera’s heading to Vegas for Ashlee’s show, I might just have to clear my calendar too. And hey, maybe even pull out some of my old studded belts. Just for old times’ sake.