What Was Cool during high school . . . 

1996
Biggest single........................................................................................Los Del Rio, "Macarena (Bayside Boys Mix)" Album of the year..................................................................................Alanis Morissette, "Jagged Little Pill"
Highest-grossing movie.........................................................................Independence Day
Popular TV shows..................................................................................ER
Superbowl XXX champs........................................................................Dallas Cowboys
President................................................................................................Bill Clinton
Top Stories.............................................................................................Olympics - Women's gymnastics

1997
Biggest single.............................................................................Elton John, "Candle In The Wind 1997"
Album of the year.......................................................................Spice Girls, "Spice"
Highest-grossing movie..............................................................Titanic
Superbowl XXXI champs............................................................Green Bay Packers
Top Stories..................................................................................Tragic Death of Princess Diana

1998
Biggest single.......................................................................Next, "Too Close"
Album of the year................................................................."Titanic" soundtrack
Highest-grossing movie........................................................Armageddon
Popular TV show...................................................................Seinfeld
Superbowl XXXII champs....................................................Denver Broncos
Top Stories............................................................................Unraveling of Monica Lewinsky Scandal

1999
Biggest single...........................................................................Cher, "Believe"
Album of the year.................................................................... Backstreet Boys, "Millennium"
Highest-grossing movie.......................................................... Star Wars: Episode I - The Phantom Menace
Popular TV shows....................................................................Who Wants to Be a Millionaire?, TRL
Superbowl XXXIII champs......................................................Denver Broncos
Top Stories...............................................................................Columbine High School tragedy, death of JFK Jr., Y2K

2000
Popular songs............................................................."Maria Maria"/"Music"/"Come On Over Baby"
Album of the year.......................................................'N Sync, "No Strings Attached"
Highest-grossing movie..............................................Mission: Impossible II
Popular TV shows.......................................................Dawson's Creek, Friends, Wrestling
Superbowl XXXIV champs.........................................St. Louis
Top Stories..................................................................Napster, Harry Potter books, controversy surrounding Eminem

Sources:
worldwideboxoffice.com
billboard.com
superbowl.com