4. EDS, 2000 -- Cat Herding
Only a company founded by Ross Perot would create a commercial that solely revolves around cat herding. EDS was founded by Perot in 1962 — and then acquired by General Motors in 1984 and then spun off into its own independent company, and then again bought by Hewlett-Packard CO. and, as of September 23rd 2009, renamed HP Enterprise Services.
If you’re wondering, yes, Ross Perot was sold in each deal along with the company and now acts as the HP CEO’s personal cook and washer.
The commercial is completely, utterly bizarre and hilarious. To us, it made no real sense as far as the actual product, and we still had no real idea what the company did after watching it, but who cares? We laughed, we cried, we took a second to actually think about what it would be like to herd cats. Mission theoretically accomplished.
3. Yahoo, 1999 -- Hair
Oh, you just have to love the Yahoo commercials of yore. They were so good that the, “Do you, uh, Yahoo?” tagline still somehow manages to creep into our lexicon.
’99 was a good time for Yahoo. They had acquired the previous search engine powerhouse, Altavista (do you remember Altavista? Back then, it was like the only way to see a slowly-loading, pixelated nipple), sold it, and continued to grow bigger and bigger. ’99 was just the beginning, 2000 brought the dot-com boom and Yahoo was the Google of the time. Stocks were high, life was good and the Yahoo CEO wore solid gold pants as a testament of the companies’ success.
Now? Now everyone wants to buy Yahoo, but they sputter on, like an old buggy, desperately trying to race the other, newer, shinier cars in its way. But we still remember a time when Yahoo was great, and when Yahooooo meant another funny commercial about a man and his fro.

