AOL 5.0 dropped in late 1999, and for a ton of people, it was the internet. You'd pop in that free trial CD, hear the dial-up screech, and suddenly you’re in—chat rooms, AIM, message boards, all of it. Version 5 was smoother than the clunky earlier builds (AOL 4.0 hit in 1998), with faster logins, better email, and a tighter interface that didn’t feel like it was built in someone’s basement. It pushed hard with “AOL Anywhere,” trying to keep you hooked even when you weren’t at your home PC. This was peak AOL—before broadband killed dial-up and the walled garden started crumbling. If you ever waited for someone to “get off the phone so I can get online,” this version probably hits home.