The most iconic onscreen texting moments of the 2000s

Welcome to 2000s Week! We’re exploring the pop culture that shaped us at the turn of the millennium, and examining what the films, shows, and games from the era say about us then and now. It’s a little #tbt to the days before #tbt was a thing.

The 2000s are bookended by cell phones. The first BlackBerry was released in 1999, giving Hollywood’s self-important businessmen and ladies an instant shorthand for being Very Busy with Lots of Emails; in 2010, the iPhone 4’s slim, futuristic form factor had folks lining up around city blocks for Apple’s all-conquering third-gen handset. In between those mobile milestones was a decade where mainstream pop culture reckoned with the slow death of the phone call at the hands thumbs of text messaging, and battled hilariously with the aesthetics of SMS.

In 2020, stories set in the general vicinity of now, mostly written by people who’ve been using mobile/cell phones for two decades, for audiences accustomed to the visual language of texting onscreen, can usually integrate text conversations seamlessly into both script and shot. But before Sherlock and House of Cards brought the floating text message graphic to the mainstream, TV, films, and music videos regularly fumbled and occasionally succeeded at showing texting in a realistic way. 

As broken down efficiently by YouTuber Tony Zhou in 2014, cutting away from an actor reaction to a grainy flip-phone or smartphone screen isn’t an appealing option, and lingering on that shot so audiences can read the text themselves drags the pacing down. Real-life user interface (UI) designs can be a pain to license or to shoot at all, so filmmakers used anything from custom-designed CGI screens overlaid on prop phones, with varying degrees of success aesthetically and functionally, to just… making some shit up.

The early 2000s saw everything from surprisingly straightforward depictions of the utility and reality of texting, to hilariously hackneyed attempts to integrate this new everyday technology into storylines, and aggressive product placement of phones that now look like horrible tiny laptops. Gaze upon these 10 notable moments that capture the essence of texting’s awkward pop culture puberty, with unscientific assessments of how cooked their attempts at authenticity are. 

Never complain about slightly dorky fake iMessage bubbles again.

10. The Departed

Key scenes in Martin Scorsese’s 2006 Boston bloodbath rely on characters being able to text without looking like they’re texting. Silent, instant, and individual communication is an update to the dead-drops and secret messages of the classic double-agent plot (the same is true of its source material, Hong Kong crime thriller Infernal Affairs, released in 2002, though that film instead had a mole send a scattershot warning text to being sent every bricky GSM-enabled device in a given area). 

But that (spoiler) gang mole Matt Damon could send a typo-free two-word message from his jacket pocket without looking was never a teenager trying to touch-text in class with a Nokia tucked casually under the desk. (Hell, if you’re over 30 and under 45, I’ll bet you still have the muscle memory required to type “No phones” into a T9 keypad without having to look at it right now. 6-6, 6-6-6, 0, 7, 4-4…)

UI rating: Grimly functional

9. Dexter

Just like the show, the texting got worse as time wore on. In its first season in 2006, those Nokia texts are , if a little precious formatting-wise. For some reason, after that they were doing shit like this. 

It makes even less sense than the finale.

UI rating: ughhhhhhhhh

8. J-Kwon

While the trusty and indestructible Nokia 3310 was a faithful companion for many from its 2000 release onward, the Sidekick was the pre-iPhone smartphone of choice. It pops up often in 2000s teen shows, as T-Mobile went on a youth-targeting product placement rampage that lasted until . The landscape-oriented Sidekick was launched in 2002 with a screen that slid (and later swivelled) up to reveal a full QWERTY keyboard. This thing was made for texting. Just ask J-Kwon, who used his in 2004 to send a very plainly formatted “text” invite to get “Tipsy.” 

UI rating: This shit looks like a mysterious note you find in a treasure-hunting PC game from 1998

7. Sexting with Rory Gilmore

An episode in the final season of Gilmore Girls has Rory trying to sext her boyfriend Logan on her trusty Sidekick, by copying passages out of Henry Miller books. It’s one of the earliest depictions of sexting on TV that I could find (though that’s not the term used here — the word was first recorded in print media in 2005 and hit Merriam-Webster in 2012). Rory’s worldly frenemy Paris tips her off, showing off her advanced skills and noting that it’s the best form of long-distance horniness because “you can do it while you’re doing other things” — which remains true today. Paris knows all! !

While we never see the screen — looking at screens is not in keeping with Stars Hollow’s rustic aesthetic — this gets points for Rory freaking out when she doesn’t see Logan’s reply for more than a day. Because it went straight to her Saved Messages somehow! Which is a different folder from your Inbox, if I remember correctly, because in the Blackberry-flavoured haze of the pre-iMessage smartphone boom, everyone lost their minds trying to make texting more like email for some reason. 

UI rating: Invisible, and likely for the best because I’m not sure I want to know which fragments of Sexus Rory Gilmore plagiarizes 

6: “Thnks fr th mmrs”

If you want a time capsule of being a certain kind of teenager in 2007, the clip for Fall Out Boy’s “Thnks Fr Th Mmrs” might do the job. Hello, pre-superstardom Kim Kardashian making out with Pete Wentz! There’s a cheeky text in there, fired off in an enormous font by the chimpanzee director making the band’s new video-in-the-video: “Yo This band is wack” he says, with a line break after the “Yo” that bothered me even then. A LINE BREAK. I ASK YOU. IS THIS A LETTER.

The song title was actually a snarky jab at the band’s label, who had repeatedly asked them to scale down their idiosyncratically lengthy track names, but the disemvowelled sentiment mirrored the way we had to hack down words letter by unnecessary letter to fit our messages into the 160-character limit. (Never forget that Twitter’s original 140-character cutoff existed because “microblogging” was created with SMS-based posting in mind. Texting is actually to blame for… so much.)

UI rating: Wack

5. The O.C.

The Sidekick also played a part in an (also heavily promotionally-considered) 2005 arc on The O.C., which saw uber-dad Sandy Cohen brandishing mean girl at Dean Hess, and informing the unlucky predator that it also has a camera phone, don’t you know? Cha-ching. (MMS, and the photo sharing it facilitated, had its first boom in the middle of the decade. My earliest grainy nudes are still out there somewhere, trapped on a Motorola Razr my ex lost in the back of a cab.)

Look upon this email-ass-looking nawty text, and be grateful for the ease with which we can now be horny without feeling like we’re filling out an online form.

UI rating: SPARKLY but also strangely businesslike

4. Gossip Girl

The first year that Americans actually sent more text messages than they made phone calls — the same year the iPhone launched. It’s also the year Gossip Girl premiered. Having never read the 2002-onwards book series, I don’t know how phone-centric it was. But I literally cannot imagine what this show would have been without the constant makeshift surveillance of wealthy teenagers’ ubiquitous phones — all the better for tipping off the titular teen Gawker, receiving the “blasts” that “she” sent out, and even appearing to catch her in the act? 

Scenes like this one captured with unusual accuracy the way phones had already become central to navigating adolescent social circles, right down to using precious mobile data to scan tiny, janky mobile Facebook profiles for info.

UI rating: Weirdly normal, unlike the characters

3: A Cinderella Story

The recent TikTok meme of Hilary Duff typing “LOL” into a purple flip phone in 2004’s A Cinderella Story is from a scene where she’s texting her mysterious internet penpal, who is lurking obliviously just feet away on his manly blue phone. Does she have his number? Is she doing ? (AIM had been around since the late ’90s, but the 2002 Sidekick was the first to integrate it with a phone, further blurring the line between IM and SMS, especially for adult screenwriters who may not have given a shit which was which.) 

Why does her reply appear randomly in the middle of the screen of his steely Samsung, but her INPUT screen is so aggressively practical?

But the icing on this particular post-Y2K cupcake is the iconic moment where she translates “LOL” for the audience in voiceover: “Laugh out loud.” It is an imperative. You cannot help but obey.

UI rating: Chaotic

2. School Of Rock

In the opening sequence of Richard Linklater’s otherwise flawless 2003 film School Of Rock, we have an example that gets it wrong and right at the same time. Jack Black’s terrible band are sweating it out in a shitty club, and a displeased punter whips out a chunky, laptop-like Nokia Communicator to text his friend: “These guys suck. Leave?” But smash that pause button, and would you look at that? It’s a WORD PROCESSOR DOCUMENT, folks. “Document03,” to be precise, and that text is just a sentence fragment in 48-point font. 

On the one hand, the “bail?” text is to this day one of the most important functions of text messaging. On the other, it says “Document03” up the top. How hard would it have been to change the document title to “Steve” to make it look even slightly more like he was texting a person instead of writing a note to himself? Was Linklater too busy that year shooting five days’ worth of Boyhood? 

UI rating: It looks like you’re trying to send a text. Do you need some assistance?

1. “Dilemma”

No matter what they did, no other piece of pop culture could top this list. In the extremely 2002 clip for this 2002 single, a pining Kelly Rowland is notoriously shown getting a “text” on her phone (another Nokia Communicator), presumably from the boo she is with while being crazy over Nelly. She is maddened! Aggrieved! Torn! She snaps the Nokia shut, which is fine, because we all know 2000s Nokias can take a beating. 

The “text” is… in a cell of a Microsoft Excel spreadsheet. 

When it became a meme again in the 2010s, Rowland and Nelly were both asked about it on TV, which must have been a nice break from talking about Beyoncé and Band-Aids, respectively, and Rowland confessed to . 

This moment lives rent-free in the heads of thousands of millennials. The sheer laziness of it. The pointlessness of 11-point all-caps on a busy, pixelated grid the camera can’t even focus on all at once, instead of the actual message screen. The ALL-CAPS, as though whichever poor PA was responsible for typing in that message couldn’t find the caps lock button and said “Fuck it.” It will haunt me with its blindingly perfect wrongness until the end of my days.

UI rating: The finest thing I’ve ever seen