Top Hip-Hop Songs From the Year You Graduated High School

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.