For NFL players, competing in the Super Bowl offers the chance of a lifetime—an opportunity to shine under the bright lights of this spectacular sporting event. And for many companies that yearn to reach the millions of TV viewers watching the big game, a 30-second TV commercial during the telecast is also a rare opportunity to strut their stuff on an international stage.

Yet like many of those football players who wilt under the Super Bowl’s intense spotlight, so too can a company’s future if its commercial fails to grab viewers’ attention or generate buzz, and ends up as a colossal waste of money. (Thirty-second spots are running around $2.6 million this year.) With IT-related companies, the ability to get their message out to the masses can be that much harder. Translating what, say, EDS does into a 30-second spot that entertains and enlightens is infinitely harder than the marketing rigors that Budweiser faces.

That’s not to say IT companies and e-commerce players haven’t given it the old college try over the years: Witness the year 2000, the apex of the dotcom boom, when the Super Bowl featured 17 dotcom commercials. We all know what happened to many of those companies shortly thereafter.

So for your enjoyment and a bit of nostalgia, CIO.com rated the 10 best and 10 worst IT Super Bowl commercials, starting way back with Xerox’s "It’s a Miracle" spot in 1977, all the way up to Careerbuilder.com’s “Working with Monkeys” spot in 2006. We used three means of analysis to differentiate the best from the worst. First, we borrowed a rule of thumb from legendary ad pundit Bob Garfield. He said, in his Super Bowl roundup last year, that an organization’s purpose for running a Super Bowl spot “is about selling messages and strategy and reaching the consumer.” Second, over-the-top attempts at humor just as often fall flat; there’s something to be said for subtlety and clever visuals. Third, we must admit to a soft spot for monkeys.

A special thanks to two websites, where you can view the commercials listed below: SuperbowlAds.com and iFilm. Here they are, in chronological order, the 10 best and 10 worst IT-related Super Bowl commercials of all time.

THE 10 BEST

1977
The Company: Xerox
What It Does: Document management technology and services enterprise
The Super Bowl Ad: It’s a Mircacle
The Gist: Brother Dominic toils painstakingly over a manuscript with a quill pen, while monkish chants intone in the background at the apparently medieval monastery. Brother Dominic presents his finished work to his superior who praises him highly and then says, “Now, I just need 500 more sets.” Near despair, Brother Dominic has a sudden idea and, racing from the cloister, enters a bright white room dominated by the Xerox 9200 Duplicating System. There, experts explain the mammoth copier and get him his stack of copied manuscripts. He delivers them to his superior, whose heavenward reply is: “It’s a miracle.” Not only did this ad win awards all over the place, it was one of the earliest examples of information technology advertising at the big game.