No other era gave us a better soundtrack for graduating school or getting dumped for the first time.
Boyz II Men, "End of the Road"
The "no, please, this cannot be the end, please take me back" goodbye.
Green Day, "Good Riddance (The Time of Your Lfie)"
The "I am really going to miss this long-running sitcom" goodbye.
Semisonic, "Closing Time"
The "you are drunk and need to call a car service" goodbye.
Madonna, "This Used To Be My Playground"
The "wistfully embracing the inevitability of aging" goodbye.