Gap's Most Iconic Commercials

In honor of the megabrand’s new campaign, we unearth our favorite ads from the past.

In honor of Gap’s shiny--actually, rugged--new campaign, we thought we’d take a look back at some of our favorite ads from the brand’s past. From the ‘90s to the holidays, check out our favorites below. Beware, you may have some of these jingles, covers and slogans in your head for the rest of the day, but that’s all part of taking a walk down memory lane.

$15.95 Will Go a Long Way at Christmas
I found this commercial a very long time ago, it’s actually older than I am. But come on, you can’t help but laugh at everything going on here—Santa, the models, it’s all so wonderfully ‘80s.


Fall into the Gap, Featuring Run DMC
Who could forget the iconic “fall into the gap” commercials? There were several out and about in their heyday, but none were as memorable as this—Run DMC in gap hoodies? It’s classic.


Everybody in Vests
Remember the fleece vest craze of the ‘90s? I certainly do, and by remember, I mean I still have mine from the Gap. And there’s definitely some Old Navy performance fleece hanging around my attic. Admittedly, this commercial was one of my first advertising loves and if DVR existed back in the day, I’d rewind and watch it again. Hooray for singing models!


Everybody in Cords
Alright, it’s worth noting that this commercial stars now-famous Parks and Recreation actress Rashida Jones (also, while we’re on the ‘90s, remember her in Boston Public?). Couple that with “Mellow Yellow” and I’m sold.


The Boyfriend Trouser
Claire Danes has tried to steal my pants many times. That’s not true, but this is a great ad and very characteristic of Gap with a classic song, dancing and a cute-but-not-sweet premise.


The Skinny Black Pant
Who can resist Audrey Hepburn? Who can resist AC/DC? Exactly.


I Love My Comfy Sweater!!
I despised this commercial until about 19 seconds in when that little girl just screams her head off...for no apparent reason. That brought it into the “it’s so crazy, it’s good” zone. It actually landed in my inbox a few weeks ago with the subject line “Christmas in July.”


Where You Get them Jeans?
Here’s Madonna’s second appearance on our countdown, this time with Missy Elliot. Everything about this screams nostalgia to me, the vests, the hoodies, the fits, everything. I think the best part is when the three kids on the sidewalk say, “Where you get them jeans?” because I definitely said that in that exact voice several times, back in the day. I am now going to say it for the rest of the day.


Pardon Our Dust
You’ve probably never seen this commercial, not many people have. It only ran in Seattle. But it’s probably one of my favorite commercials of all time. You know a brand has some solid minds behind it when they’re able to make fun of themselves. Here, they play on the image of Gap as that oh-so-neat and tidy store in your neighborhood. Extra points for the crash scene. Well played.


Pico Creative Loft
And here it is, the new face of Gap...on your TV. Take a trip to downtown L.A. to find out exactly where your blue jeans are coming from, meet the designers, watch the process and get a glimpse of just how cool the Gap can be. Will this new venture be an instant-classic like the above? That remains to be seen, but I’ll rest a little easier at night knowing Gap jeans come from “the last stronghold of denim.”

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