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"Cry Me A River" — Justin Timberlake (2002)
It required so much more arm strength to film a revenge make-out session before iPhones.
"Leave (Get Out)" — JoJo (2004)
Yes, JoJo, drop that Nokia brick; it'll bring you nothing but heartache.
"The Boy Is Mine" — Brandy & Monica (1998)
This isn't just a love triangle, it's a tech triangle — corded, cordless, and ancient-looking flip phones are all involved.
"Us Against The World" — PLAY (2001)
Yes, this video gets futuristic, but it represents a real time in tech when every kid wanted a completely unimpressive robot dog. Also, when purple camo was super in.