The 1990s was a decade with a lot of major events. Argumentably, the biggest and swellest decade in Drewland history:
- January 1: Drewland broadcasts a Happy New Year 1990 during this day and New Year's Eve 1989.
- July/August: Drew Pickles makes a 2nd pilot for his show, being a sequel to the one made in November 1989.
- September 20: Blame! releases their album.
- January 4: The Wiggles are resurrected.
- February 3: Angelica Pickles was born.
- May 1: The Village Boiz release their first grunge album.
- August 11: Drew Pickles' show, which was renamed as Rugrats, first aired on Logo.
- September 24: Nirvana's album Nevermind gets released, causing a viral impact on Drewland.
- September 30: Jerry Springer first airs his show on Logo.
- February 1: Drew Pickles and Barney announce that grunge must be everywhere.
- April 16: Hikaru Gosunkugi was born.
- April 29: Drewland started to undergo an invasion of chimpanzees and monkeys that broke loose from the Los Angeles zoo.
- July 3: Ripper Roo and C-3PO get arrested for dressing as boxes, raping many boys, and forcing Wal-Mart to play Nirvana and Soundgarden.
- September 22: Beavis' pilot air on Logo.
- November 17: Beavis airs his second pilot on Logo.
- January 20: Bill Clinton goes to office. Drew Pickles had to become a vice president. Many cities in Drewland, especially New Harlem, welcomed him.
- February 4: Jerry Springer saw Moon Man bashing Jewish people on his show, causing many Drewlanders to get in rage, especially Lou Pickles.
- March 8: Beavis officially airs his show on Logo.
- June 13: John Marston was murdered by The Straight King.
- September 13: Kurt Cobain releases his ultra swell In Utero.
- September 18: Rocko, Filburt, and Heffer first aired their show on Logo.
- September 22: Dr. Robotnik saying "pingas" goes viral, causing Drew Pickles, Bill Clinton, and Barney to force him to join the Barney Bunch.
- October 10: A 5 year old watched Beavis on Logo and thought fire was fun. Beavis nearly had to cancel his show because of this.
- November 1: Logo changes their logo used from 1984 to 1993.
- December 24: Many Drewlanders came to see Ronald McDonald's Christmas tree. It was seen on Logo.
- January 3: Ronald McDonald gets his 3rd tattoo, which mainly shows a heart with Grimace on it.
- April 5: Kurt Cobain attempts to commit suicide and shockingly, he survives.
- April 8: Kurt Cobain's electrician joins the Barney Bunch.
- September 16: Ripper Roo's bratty and homophobic daughter Tawna was born.
- November 23: Dick the Clown and Crash Bandicoot join the Barney Bunch.
- May 20: The Painter asks Drew Pickles if he could join the Barney Bunch, and sadly, he had to wait until 1997 or 1998 to find out the results.
- September 29: The ultra-swell PS1 comes out.
1996 was a very cynical year for Drewland.
- Mid 1996: Fresh Prince gets cancelled.
- September 13: Tupac dies a sad death.
- November 24: A magnitude 6.8 earthquake hits O-Town, killing over 90,000 people. Rocko was one of the only survivors. He joined the Barney Bunch 2 weeks later.
- December 5: Ren and Stimpy nearly die of a stroke after smacking their heads with a hammer while playing "Happy Happy Joy Joy".
- January 11: Ripper Roo, Trent Lane, C-3PO Fag Bot, and Ken join the Barney Bunch.
- January 25: Ripper Roo airs his show on Logo.
- April 27: Ripper Roo and Drew Pickles declare grunge to be dead.
- August 7: Qui-Gon Jinn commits suicide. Anakin Skywalker replaces him as lead singer of Blame!.
- August 29: The Straight King kills Timmy Turner, Timmy Turner's father, and Dinkleburg right near a local Burger King in Drewland. This caused an outrage for many Drewlanders and McDonalds workers.
- August 30: All Burger Kings in Drewland were destroyed.
- November 26: Ripper Roo goes on Maury for a paternity test to see if he's Tawna's father.
- April 20: Eric Harris and Dylan B. Klebold fail to achieve their high score at Columbine High School and end up shoving Tec 9s and Carbines up their asses, resulting in their arrests, imprisonment, and national attention.