Depending on your age, high school was either a really long time ago or a recent memory. Either way, just thinking back to those days unlocks a lot of memories. Whether it's getting good grades or needing a study buddy to help through the struggle, joining extracurricular activities or becoming a team player in a sport, hanging out with friends or chilling at parties, there are plenty of cherished times. Music plays a part in serving as a soundtrack for moments like this, especially hip-hop. With the growth of the genre over the last 25 years, a many hip-hop songs soundtracked plenty of high school memories. As students rock their cap and gown to graduate in June, XXL documents the top hip-hop songs (according to the Billboard Hot 100) from the year you graduated high school—specifically 1996 to 2021.

The late 1990s were a great time for hip-hop, as anyone who was in their teen years back then can attest to. In early June of 1996, Bone Thugs-N-Harmony's "Crossroads" was the No. 1 song in the country on the Billboard Hot 100. The track dedicated to the group's fallen friends, including Eazy-E, resonated with listeners for its stirring vocals, becoming the highest-debuting rap single at the time of its release. The second top hip-hop song on the Hot 100 in early June was MC Lyte's "Keep On, Keepin' On" featuring Xscape (From Sunset Park) at No. 18.

A year later in 1997, Bad Boy Records, founded by Diddy, and with the late great The Notorious B.I.G. as its leading rapper, dominated the airwaves. Biggie's timeless single "Hypnotize" was the No. 4 song in the country, and Diddy's "Can't Nobody Hold Me Down" featuring Bad Boy's youngest in charge, Ma$e, was at No. 15. This perfectly encapsulates the times, as the storied record label's music everywhere, and rightfully so. These songs are etched in the memories of multiple eras of rap fans, and without a doubt, took over plenty of high school events.

The South has been on a crazy run as it comes to rap relevance, and this was true long ago, even back in 2006. In early June of that year, Chamillionaire's "Ridin'" featuring Krazyie Bone was the top song on the Hot 100, and Lil Jon's "Snap Yo Fingers" with E-40 and Sean Paul (of YoungbloodZ fame) was just a few spots down at No. 7. Chamillionaire was a Houston mixtape legend before he ever took off commercially, and when it was his time to shine, "Ridin'" became inescapable. Then, as it comes to Lil Jon, he's one of the most important producers in rap history. The Crunk King's influence is still felt in hip-hop (and beyond) to this day. "Snap Yo Fingers" charting so well and being so big 15 years ago is just another glimpse of how vital Lil Jon is to the South's rise into mainstream hip-hop.

Check out the list below to find your favorite high school jams or get hip to some ones that were before your time. Here are the top hip-hop songs from the year you graduated high school.

  • 1996

    Bone Thugs-N-Harmony's "Crossroads" at No. 1

    MC Lyte's "Keep On, Keepin' On" featuring Xscape (From Sunset Park) at No. 18

  • 1997

    The Notorious B.I.G.'s "Hypnotize" featuring Pam Long at No. 4

    Diddy's "Can't Nobody Hold Me Down" featuring Ma$e at No. 15

  • 1998

    Busta Rhymes' “Turn It Up (Remix)” / “Fire It Up” at No. 17

    Will Smith's “Gettin' Jiggy Wit It” at No. 18

  • 1999

    JT Money's "Who Dat" featuring Sole at No. 9

    Will Smith's “Wild Wild West” featuring Dru Hill and Kool Moe Dee at No. 14

  • 2000

    Eminem's “The Real Slim Shady” at No. 7

    Jay-Z's “Big Pimpin” at No. 23

  • 2001

    Nelly's "Ride Wit Me" featuring City Spud at No. 5

    Missy Elliott's "Get Ur Freak On" at No. 9

  • 2002

    Diddy's "I Need A Girl (Part One)" featuring Usher and Loon at No. 2

    Fat Joe's "What's Luv" featuring Ashanti at No. 3

  • 2003

    50 Cent's "21 Questions" featuring Nate Dogg at No. 1

    Busta Rhymes and Mariah Carey's "I Know What You Want" featuring Flipmode Squad

  • 2004

    Twista's "Overnight Celebrity" at No. 6

    Petey Pablo's "Freek-A-Leek" at No. 10

  • 2005

    50 Cent's "Just A Lil Bit" at No. 4

    The Black Eyed Peas' "Don't Phunk With My Heart" at No. 5

  • 2006

    Chamillionaire's "Ridin'" featuring Krayzie Bone at No. 1

    Lil Jon's "Snap Yo Fingers" featuring E-40 and Sean Paul of The YoungBloodZ at No. 7

  • 2007

    Timbaland's "Give It To Me" featuring Justin Timberlake and Nelly Furtado at No. 4

    Huey's "Pop, Lock & Drop It" at No. 6

  • 2008

    Lil Wayne's "Lollipop" featuring Static Major at No. 1

    Plies' "Bust It Baby Part 2" featuring Ne-Yo at No. 14

  • 2009

    The Black Eyed Peas' "Boom Boom Pow" at No. 1

    Kid Cudi's "Day 'N' Nite" at No. 7

  • 2010

    B.o.B's "Airplanes" featuring Hayley Williams at No. 2

    B.o.B's "Nothin' On You" featuring Bruno Mars at No. 5

  • 2011

    Pitbull's "Give Me Everything" featuring Ne-Yo, Afrojack and Nayer at No. 3

    Black Eyed Peas' "Just Can't Get Enough" at No. 4

  • 2012

    Nicki Minaj's "Starships" at No. 5

    Flo Rida's "Wild Ones" featuring Sia at No. 6

  • 2013

    Macklemore and Ryan Lewis' "Can't Hold Us" featuring Ray Dalton at No. 1

    Macklemore and Ryan Lewis' "Thrift Shop" featuring Wanz at No. 11

  • 2014

    Iggy Azalea's "Fancy" featuring Charli XCX at No. 1

    Pitbull's "Wild Wild Love" featuring G.R.L. at No. 36

  • 2015

    Wiz Khalifa’s “See You Again” featuring Charlie Puth at No. 1

    Fetty Wap's “Trap Queen” at No. 3

  • 2016

    Drake's "One Dance" featuring Wizkid and Kyla at No. 1

    Desiigner's "Panda" at No. 2

  • 2017

    DJ Khaled's "I'm The One" featuring Justin Bieber, Quavo, Lil Wayne and Chance The Rapper at No. 3

    Kendrick Lamar's "Humble." at No. 5

  • 2018

    Drake's "Nice For What" at No. 1

    Childish Gambino's "This Is America" at No. 2

  • 2019

    Lil Nas X's "Old Town Road" featuring Billy Ray Cyrus at No. 1

    Post Malone and Swae Lee's "Sunflower" at No. 6

  • 2020

    Megan Thee Stallion's "Savage" at No. 2

    DaBaby's "Rockstar" featuring Roddy Ricch at No. 3

  • 2021

    Doja Cat's "Kiss Me More" featuring SZA at No. 5

    Polo G's "Rapstar" at No. 6

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