In addition to the commentary on specific events, each year's episode also has all of the following segments.Then and Now: Emma Bunton presents a comparison of trends in the given year and the present day.
Pimpest Tracks: Ben Stein presents a list of the popular rap music songs of the year.
Guys We'll Go Gay For: Jay and Silent Bob present a list of male celebrities or fictional characters from each year.
Bootyfone: The announcer of Moviefone, Russ Leatherman, lists the three songs most conducive to a romantic environment.
90210 Lost Diary: A summary of the events in the TV series Beverly Hills, 90210 is read from a journal, ostensibly from the point of view of Andrea Zuckerman.
College Radio Cut: A. Jay Popoff and Jeremy Popoff of the rock band Lit discuss the college rock song of the year.
Bell Biv DeVoe's "Poison"
2 Live Crew
Paula Abdul's "Opposites Attract"
James "Buster" Douglas' defeat of Mike Tyson
Days of Thunder
The Fresh Prince of Bel-Air
Dick Tracy/Madonna's "Vogue"
Moscow gets its first McDonald's
Arnold Schwarzenegger in Total Recall and Kindergarten Cop
Raw: Michael Ian Black on 90's fans
Ben Stein's Pimpest Tracks of 1990: "911 is a Joke" by Public Enemy, "100 Miles and Runnin'" by N.W.A and "I Left My Wallet in El Segundo" by A Tribe Called Quest
Guys We'll Go Gay For: Arnold Schwarzenegger and Keifer Sutherland
Bootyfone: "Come Back to Me" by Janet Jackson, "Close to You" by Maxi Priest and "All I Wanna Do Is Make Love to You" by Heart
College Radio Cut of 1990: "The Summer" by Yo La TengoRobin Hood: Prince of Thieves
Public Enemy and Anthrax's "Bring Tha Noize"
Soviet Union goes out of existence
Terminator 2: Judgment Day
Chris Isaak's "Wicked Game"
The Atlanta Braves Tomahawk Chop controversy
Starter Jackets/Pagers and their use for numeric spelling
Red Hot Chili Peppers' "Give It Away" and Weird Al's parody version
Wilt Chamberlain's A View From Above
Extreme's "More Than Words"
Ben Stein's Pimpest Tracks of 1991: "Summertime" by DJ Jazzy Jeff & The Fresh Prince, "Can't Truss It" by Public Enemy and "Jackin for Beats" by Ice Cube
Guys We'll Go Gay For: Val Kilmer and Kevin Costner
Bootyfone: "I Adore Mi Amor" by Color Me Badd, "I Can't Wait Another Minute" by Hi-Five, "Because I Love You (The Postman Song)" by Stevie B
College Radio Cut of 1991: "Dirty Boots" by Sonic Youth
Raw: Michael Ian Black on Wilt ChamberlainThe Crying Game
House of Pain's "Jump Around"
Men Are from Mars, Women Are from Venus
Mr. Big's "To Be With You"
The nicotine patch
Bill Clinton says he "didn't inhale"
Body Count's "Cop Killer"
Mad About You
George H.W. Bush vomits on Japan's prime minister
Larry Bird retires
Sinéad O'Connor rips a picture of the Pope on Saturday Night Live
A League of Their Own
Teen Talk Barbie
White Men Can't Jump
Ben Stein's Pimpest Tracks of 1992: "Set Adrift on Memory Bliss" by P.M. Dawn, "Flavor of the Month" by Black Sheep and "They Want EFX" by Das EFX
Guys We'll Go Gay For: Matt Dillon and Wesley Snipes
Bootyfone: "Masterpiece" by Atlantic Starr, "Forever in Love" by Kenny G and "Save the Best for Last" by Vanessa Williams
Raw: Hal Sparks on Bush barfs
College Radio Cut of 1992: "Push th' Little Daisies" by WeenCliffhanger
The Proclaimers' "I'm Gonna Be (500 Miles)"
The Chicken Soup For The Soul series
The U.S. military's "Don't ask, don't tell" polite
Monica Seles gets stabbed
Cypress Hill's "Insane in the Brain"
What's Eating Gilbert Grape
Great Flood of 1993
Frank Sinatra's Duets
Animaniacs/Pinky and the Brain
Ben Stein's Pimpest Tracks of 1993: "Slam "by Onyx, "Passin' Me By by The Pharcyde and "Rebirth of Slick" by Digable Planets
Guys We'll Go Gay For: Sylvester Stallone and Robert Redford
Bootyfone: "Knockin' Da Boots" by H-Town, "Again" by Janet Jackson and "One Last Cry" by Brian McKnight
College Radio Cut of 1993: "My Name is Mud" by Primus
Raw: Rachael Harris on ZimaThe Wonderbra
Anna Nicole Smith marries J. Howard Marshall
Tales From The Crypt (originally premiered in 1989)
Michael Fay's caning
Benedictine Monks' Chant
The Adventures of Priscilla, Queen of the Desert
New York Rangers win the Stanley Cup
Natural Born Killers
Ben Stein's Pimpest Tracks of 1994: "Keep Ya Head Up" by 2pacI , "U.N.I.T.Y." by Queen Latifah and "Fantastic Voyage" by Coolio
Bootyfone: "Bump n' Grind" by R. Kelly, "I Wanna Be Down" by Brandy and "I Swear" by All-4-One
College Radio Cut of 1994: "Cut Your Hair" by Pavement
Guys We'll Go Gay For!: Woody Harrelson and Dante or RandallThe Usual Suspects
Psychic Friends Network
Newt Gingrich vs. women in the military
The hemp debate
Montell Jordan's "This Is How We Do It"
To Wong Foo, Thanks for Everything! Julie Newmar
Six Degrees of Kevin Bacon
O.J. Simpson murder trial
Raw: Juliette Lewis on Shaggy
Ben Stein's Pimpest Tracks of 1995: "Player's Anthem" by Junior M.A.F.I.A., "I Wish" by Skee-Lo and "Big Poppa" by Notorious B.I.G
Guys We'll Go Gay For!: Patrick Swayze and Tom Hanks
Bootyfone: "Water Runs Dry" by Boyz II Men, "Candy Rain" by Soul 4 Real and "Brown Sugar" by D'Angelo
College Radio Cut of 1995: "Seether" by Veruca SaltKerri Strug
The Crocodile Hunter
Romeo + Juliet
The Caesar haircut
Jeff Foxworthy's redneck routine
Busta Rhymes' "Woo Hah!! Got You All in Check"
Pamela Anderson and Tommy Lee's sex tape
Deion "Primetime" Sanders
East Coast-West Coast hip hop rivalry
David Crosby fathers Melissa Etheridge's child
R. Kelly's "I Believe I Can Fly"
Raw: Modern Humorist on Kerri
Ben Stein's Pimpest Tracks of 1996: "Sure Shot" by Beastie Boys, "California Love" by 2Pac feat. Dr. Dre and "Tha Crossroads" by Bone Thugs-n-Harmony
Guys We'll Go Gay For: Leonardo Di Caprio and Ving Rhames
Bootyfone: "Don't Let Go (Love)" by En Vogue, "You're Makin Me High" Toni Braxton and "No Diggity" by BlackstreetL
College Radio Cut of 1996: "What I Got" by SublimeAir Force One
Kenny G breaks the world record for longest note held
Meredith Brooks' "Bitch"
"Death" of Joe Camel
The beginning of ratings for TV shows (e.g. "TV-MA", "TV-14", "TV-PG")
Marcy Playground's "Sex and Candy"
Latrell Sprewell chokes his coach and Marv Albert bites his girlfriend
The death of Chris Farley
Mary Kay Letourneau
Sugar Ray's "Fly"
Pokémon (the show did not debut until in 1998)
Barbie and Paula Jones get makeovers
Guys We'll Go Gay For: Harrison Ford and George Clooney
Ben Stein's Pimpest Tracks of 1997: "Let Me Clear My Throat" by DJ Kool, "Been Around the World" by Puff Daddy & the Family and "No Diggity" by Blackstreet
Raw: Patrice O'Neal on Marv Albert
Bootyfone: "You Make Me Wanna" by Usher, "In My Bed" by Dru Hill and "Nobody" by Keith Sweat
College Radio Cut of 1997: "All Is Full of Love" by BjörkGodzilla
Ginger Spice leaves the Spice Girls
Alanis Morissette's "Thank U"
Buffy the Vampire Slayer (originally premiered in 1997)
Lay's WOW chips
Mad cow disease
Gary Coleman punches a fan
MTV's guest VJ Jesse Camp
Pras' "Ghetto Supastar (That Is What You Are)"
Behind the Music
The Prodigy's "Smack My Bitch Up"
Naomi Campbell throws a cell phone at an assistant
Run Lola Run
Raw: Michael Ian Black on Raves
Ben Stein's Pimpest Tracks of 1998: "I Got the Hook Up" by Master P, "Find A Way" by A Tribe Called Quest and "Intergalactic" by Beastie Boys
Guys We'll Go Gay For: Adam Sandler and Kevin Bacon
Bootyfone: "Lately" by Divine, "All My Life" and K-Ci & JoJo and "The Boy is Mine" by Brandy and Monica
College Radio Cut of 1998: "Sexy Boy" by AirFreaks and Geeks
Jay-Z's "Hard Knock Life"
Matthew McConaughey arrested for playing the congos naked
The Tom Green Show
Win Ben Stein's Money
Being John Malkovich
Raw: Juliette Lewis on Jay-Z
Ben Stein's Pimpest Tracks of 1999: "Can I Get A..." by Jay-Z, and "Party Up" by DMX and "Love is Blind" by Eve
Guys We'll Go Gay For!: James Van Der Beek and Jason Biggs
Bootyfone: "Angel of Mine" by Monica, "Back at One" by Brian McKnight and "The Hardest Thing" by 98 Degrees
College Radio Cut of 1999: "My Own Worst Enemy" by Lit