AOL AOL

AOL, once the grandmaster of dial-up dreams, was founded in 1983 by Steve Case and a gang of visionaries who thought a floppy disk with “You’ve Got Mail” would be the key to the Internet's future. Known for its once-ubiquitous CDs that littered mailboxes like confetti, AOL was the 1990s' digital gateway drug—ushering millions into the World Wide Web and simultaneously proving that it was possible to combine glacially slow internet with exorbitant subscription fees. The company's zenith came in 2000 with the $165 billion merger with Time Warner, a deal that was less a marriage and more a collision of ego-driven behemoths—resulting in a spectacularly acrimonious divorce. Today, AOL's valuation is a shadow of its former self, slipping into obscurity amidst scandals over privacy breaches and questionable business practices. Under the stewardship of Tim Armstrong, who led the charge in trying to revive the brand with high-profile acquisitions like the Huffington Post, AOL has become a relic of a bygone era—fondly remembered for its clunky interface and incessant pop-ups, but largely dismissed in the digital age as a punchline.