Today, Adobe Illustrator—in practical terms the last vector-graphics drawing application standing (on its feet, anyway)—turns 25 years old. Even tho it now turns out to be the oldest, Illustrator wasn’t the first. MacDraw, Cricket Draw, and a host of others had stakes in the ground before it came along. But Illustrator was the first to print reliably to PostScript RIPs, which meant that nothing dropped out and strokes aligned just as you had hoped. And it included a GUI for laying down Bézier curves, known forevermore with love and loathing as the Pen tool.

At the time of its release (1987), the only other program with a Pen was Fontographer, an excellent typeface-creation program from the folks who would a few months later give Illustrator a run for its money with Aldus FreeHand.

Just for fun, here’s the first vector illustration I drew (also c. 1987) in the black and white-only and Macintosh-only Illustrator 1.0.

Just for larfs, here’s how that same image appeared on a Mac 512K screen, which is what we all were using in those dim days. On the plus side, you could enjoy this splendid preview only when you hard-switched to the Preview mode. Which didn’t let you draw, btw. You had to just sit there in awe of your creation. Oh, wait, on second thought, that actually sucked!

Lest anyone forget, 512K is roughly enough RAM to hold a full-color image that measures 418 x 418 pixels. (In the name of all that’s holy, how in the world did we manage?) And yet Illustrator worked without a hiccup.

(Warning: cursing ahead.)

As a trade artist, I reveled in Illustrator 1.0. But as a budding trainer, I ignored it. (The first third-party book that covered Illustrator—head-to-toe in six chapters!—was the product of Tony Bove and Cheryl Rhodes.) Instead, I focused my energies on the first book on what appeared to be the superior full-color, gradient-imbued, and arguably easier-to-use drawing program, FreeHand. And, frankly, there were a lot of things FreeHand did back-in-the-day better than Illustrator does now: coordinate anchor-point positioning, the ability to join text to a path, simpler clipping masks . . . well, it’s a long list.

Just to cover my bets, I wrote a book about Illustrator 88 (a.k.a 2.0), and I’ve never missed a version since. By which I mean, I wrote books on versions 3 thru 8 (not to mention v.1 on the PC, what a dog!) and recorded videos on Illustrator 9 all the way to the modern CS5. I even wrote a book on CS5.

It wasn’t always smooth sailing. I remember a shouting match with the product manager of Illustrator 6 on the Knife tool, which remains a shockingly crappy piece of shit. (If you want to experience its horribleness first hand, you’ll find it in the Eraser tool flyout menu.) But starting with Illustrator 9, when things went dynamic, the program suddenly blossomed. And that’s when Illustrator and I got, well, you know, kinda serious.

Yes, it’s a big floppy program. Yes, the simple act of joining two paths is enough to make you break your keyboard into pieces (as you repeatedly smash the J key and cry, “Join, you fucking piece of shit, join!”). Yes, it’s interface is complete and utter mayhem. But Illustrator is powerful like a nuclear submarine is powerful. And rickety. And possibly capable of going off on its own and killing everyone in a 100-mile radius.

By which I mean, once you come to love it, there’s no going back.

(What oh what on the face of the mother-fucking planet do I have to do to make you join?!)