20 Years of Monkey Business: A Flashback to 2005

We’ve Been Around Since 2005. Let’s Take a Trip Back.

Can you believe 2005 was twenty years ago? Neither can we. But here we are—older, wiser, and still doing what we love (only now with better fonts and stronger Wi-Fi). As we celebrate Crooked Monkey’s 20th anniversary, we figured it’s only right to rewind the tape and take a look at the world we were born into. Spoiler alert: it was weird, iconic, and kind of amazing.

Let’s Set the Scene: It’s 2005
You just updated your AIM away message. Your Motorola Razr is flashing. You’re wearing bootcut jeans and a graphic tee layered over a long-sleeve shirt. You’ve got a Fall Out Boy track blasting on your iPod Mini. Life is good.

2005 was the golden age of early tech, questionable fashion, and unforgettable music. And while some things have (thankfully) evolved—like the ability to customize swag online instead of sketching it in a notebook—others, like our love of great design and bold creativity, have stayed the same.

The Fashion: Low Rise, High Drama
Back in 2005, fashion was all about bold choices. Layering was practically a sport. You wore tank tops over polos and thought trucker hats were a personality trait (thanks, Ashton Kutcher).

Brands like Abercrombie & Fitch, Hollister, and Von Dutch ruled mall culture. Logos were loud. Belts were wide. Skirts were… barely there. And don’t even get us started on the popularity of UGG boots in 90-degree weather.

Today? We’re all about sleek, sustainable merch that people actually want to wear. But hey—without those cringey early 2000s fits, would we appreciate minimalism as much?

The Music: Emo, iPods, and the Birth of Virality
The soundtrack of 2005 was a mix of Green Day, Gwen Stefani, Kanye West (pre-Twitter chaos), and Kelly Clarkson belting out “Since U Been Gone.” Emo was mainstream, pop-punk was thriving, and MySpace Top 8 drama was real.

Meanwhile, iPods were everywhere. Remember scrolling that click wheel to find your favorite song? Streaming wasn’t even on the radar—Napster had just been shut down (again), and YouTube launched that year. Yes, 2005 gave us the very first viral cat video. The internet would never be the same.

At Crooked Monkey, we weren’t making viral TikToks (those didn’t exist), but we were already obsessed with standing out and helping others do the same. From music to merch, the vibe was always express yourself.

The Tech: Peak Dial-Up to Digital Awakening
Facebook was barely out of the dorm room. Twitter wasn’t born yet. People were still using BlackBerrys for email (and feeling fancy doing it). YouTube was brand new, and Netflix? It mailed DVDs in red envelopes.

Crooked Monkey started at this very moment of digital shift—where analog met possibility. We saw what was coming and jumped in headfirst. Twenty years later, we’ve evolved with the tech. Custom portals, integrations, automation—we’ve embraced it all to make your swag smarter and your experience seamless.

The Culture: Flip Phones, Movie Nights, and Burned CDs
2005 culture was simple—but magical. You memorized your best friend’s number. You made mixtapes for your crush. You watched The OC, Laguna Beach, and Grey’s Anatomy (season one, folks). And the Mean Girls quotes were flying.

There was no cloud storage, no Google Docs. Just flash drives and floppy disks (RIP). And somehow, despite the clunky tech, things felt… connected. Personal. Tangible.

That’s something we’ve kept in our DNA: personalization. Every piece of swag we make today still channels that sense of meaning, of “this was made for me.”

20 Years Later: We’re Still Doing It Our Way
Two decades later, we’re still bringing the same energy—just with upgraded tools and much better haircuts. From our roots in bold graphic tees to being a go-to corporate swag partner, the mission has always been the same: make things that people love.

So whether you’ve been rocking with us since the MySpace era or just discovered us via a very stylish LinkedIn post—thank you. We wouldn’t be here without the folks who believed in our weird, wonderful, make-it-custom philosophy.

TL;DR: 2005 Was Wild. We’re Still Here. And We’re Just Getting Started.
We’ve grown up, but we haven’t outgrown the fun. Because great swag—just like great memories—sticks with you.

So here’s to 20 years of creativity, chaos, and custom merch with meaning. Let’s make the next 20 even bolder.