OK, so it probably wasn’t the seal-breaking No. 1 most hip-hop fans would’ve chosen: a pop-leaning, suburbs-courting, classic rock-sampling crossover anthem from the artist born Robert Van Winkle, a white MC of controversial credibility. Still, it was a crucial chart first in rap history: the culmination of a number of smaller breakthroughs over the previous decade, and the start of many historic hip-hop No. 1s to come.

Here are 15 more of the most important rap firsts in Billboard Hot 100 history:

1. First rap Hot 100 hit: Sugarhill Gang’s “Rapper’s Delight” (No. 36, 1/12/80)

The first single to introduce hip-hop to the mainstream peaked in the Hot 100’s top 40 at the outset of the 1980s, portending the slowly building crossover influence the genre would have over the course of the decade. Quick shoutout also due to The Jaggerz’ “The Rapper,” which had nothing to do with hip-hop as a genre, but did bring “rap” in some form to No. 2 on the Hot 100 at the beginning of the 1970s.

2. First No. 1 hit with a rap verse: Blondie’s “Rapture” (No. 1, 3/28/81)

With its shuffling post-disco groove, falsetto-sung hook and rock-band makeup, you wouldn’t exactly call new wave greats Blondie’s fourth and final Hot 100 No. 1 single a rap song. But it does contain a landmark rap verse from frontwoman Debbie Harry — spitting about the “Man From Mars” and namechecking early hip-hop icons Grandmaster Flash and Fab 5 Freddy, the latter of whom also appears in the song’s music video, an early MTV favorite.

3. First rap top 10 hit: Run-D.M.C.’s “Walk This Way” (No. 4, 9/27/86)

The famous breaking down of the wall between rock and rap — literally, in the case of the song’s massively popular music video — brought rap stars Run-D.M.C. to the Hot 100’s top 10 for the first time, with a boost from Aerosmith, whose original version of the song peaked at No. 10 in 1977. It was one of many rap firsts for Run-D.M.C., who were also the first rap act played on MTV, the first rap act to appear on the cover of Rolling Stone, and the first rap act with a top 10 LP on the Billboard 200 albums chart.

4. First rap act with multiple top 10 hits: Tone Loc (“Wild Thing,” No. 2, 2/18/89; “Funky Cold Medina,” No. 3, 4/29/89)

It was Tone Loc’s year in 1989, as the slow-and-low MC became the first rapper to ever score multiple top 10 hits, both off debut album Loc-ed After Dark). The back-to-back smashes marked an unprecedented burst of pop success for a single rap artist; unfortunately, it was also the sum total of Tone’s top 40 career, as he never charted a single higher than No. 80 on the Hot 100 afterwards.

5. First rap act with a guest credit on a top 10 hit: Eric B. & Rakim (Jody Watley’s “Friends,” 8/26/89)

Six years before Mariah Carey and Ol’ Dirty Bastard set the standard for pop-meets-rap crossovers with the “Fantasy” remix, late ’80s star Jody Watley invited hip-hop duo Eric B. & Rakim to guest on her Larger Than Life single “Friends.” It resulted not only in the first top 10-charting feature for a rap artist on any single, but it also marked the legendary rap act’s sole trip together to the top 40 — the duo only scored one Hot 100 hit as lead artists, the No. 96-peaking “Juice (Know the Ledge)” in 1992.

6. First rap group with a No. 1 hit: Marky Mark & The Funky Bunch feat. Loleatta Holloway’s “Good Vibrations” (10/5/91)

Almost exactly a year after Vanilla Ice scored the first-ever rap No. 1 on the Hot 100, Marky Mark & The Funky Bunch became the first rap group to top the chart, with the Loleatta Holloway-sampling hip-house hybrid “Good Vibrations.” Marky Mark, better known as Mark Wahlberg and then most famous for being the brother of Donnie Wahlberg from New Kids on the Block, would of course go on to even greater success as a film actor in the late ’90s and ’00s.

7. First Black rap artist with a No. 1 hit: PM Dawn, “Set Adrift on Memory Bliss” (11/30/91)

Though two members of the Funky Bunch (Scott “Scottie Gee” Ross and Anthony “Ashley Ace” Thomas) were Black, Marky Mark (the only MC to actually rap on the song) was white, making it two straight No. 1s recorded by white rappers. That streak was finally broken eight weeks later, when Black New Jersey brother duo PM Dawn’s chilled-out, Spandau Ballet-sampling “Set Adrift on Memory Bliss” ascended to the chart’s top spot.

8. First rap song to top Billboard‘s year-end Hot 100: Coolio’s “Gangsta’s Paradise” (1995)

Other rap singles had gotten close: Sir Mix-a-Lot’s “Baby Got Back” finished at No. 2 behind Boyz II Men’s “End of the Road” on Billboard‘s 1992 year-end Hot 100, while Tag Team’s “Whoomp! There It Is” snagged the runner-up spot in back of Whitney Houston’s “I Will Always Love You” in 1993. But the first song to top a year-end Hot 100 was Coolio’s “Gangsta’s Paradise” in 1995, after the Stevie Wonder-sampling Dangerous Minds soundtrack single ruled the Hot 100 for three weeks that September, and spent another nine weeks at No. 2.

9. First rap artist with a guest credit on a No. 1 hit: Dr. Dre (Blackstreet’s “No Diggity,” 11/9/96)

Though Dr. Dre had long established his bonafides as one of the all-time hip-hop greats by 1996, and even scored a No. 2 hit single as a lead artist with the Snoop Dogg-featuring “Nuthin’ But a ‘G’ Thang” in 1993, his first No. 1 came as a featured artist on Blackstreet’s “No Diggity” in 1996. (Rapper Queen Pen, who also has a guest verse on the song, was not listed on its official chart credit.) Dre also could’ve notched a second No. 1 as a guest that year as part of 2Pac’s smash “California Love,” but that single topped the Hot 100 for 2Pac as a double-A side with “How Do U Want It,” and only that song’s guests (K-Ci & JoJo) were listed on the official chart credit.

10. First song with multiple credited rap artists to hit No. 1: Puff Daddy feat. Mase, “Can’t Nobody Hold Me Down” (3/22/97)

After years of putting in work behind the scenes as the founder of Bad Boy Records and the Notorious B.I.G.’s right-hand exec, Sean “Puff Daddy” Combs released his debut solo single “Can’t Nobody Hold Me Down” to immediate success in 1997. He had help, however: Bad Boy’s newest signee, Mase, was also featured on the single, marking the first Hot 100 top 10 entry for both artists, and the first Hot 100 No. 1 of any kind with multiple credited rap artists.

11. First posthumous No. 1 by a rapper: The Notorious B.I.G.’s “Hypnotize” (5/3/97)

While the irresistible “Hypnotize” was likely destined for major chart success in 1997 regardless, the song rocketed up the Hot 100 following the shooting death of the artist born Christopher Wallace that March 9th. The song bested the chart in early May, replacing Bad Boy labelmates Puff Daddy and Mase on top, becoming the first-ever Hot 100 No. 1 by a late rapper — and Biggie added a second posthumous No. 1 in August of that year, this time with Puff Daddy and Mase also in tow, on “Mo Money, Mo Problems.”

12. First rap song to debut at No. 1: Puff Daddy & Faith Evans feat. 112, “I’ll Be Missing You” (6/14/97)

Following the success of “Can’t Nobody Hold Me Down,” and the tragic death of The Notorious B.I.G., few rap singles in history had been as anticipated as Puff Daddy’s follow-up tribute to his late friend and business partner, the Police-sampling “I’ll Be Missing You.” The song unsurprisingly debuted at No. 1 — the first rap single ever to do so — and stayed there for 11 weeks, also becoming the longest-reigning hip-hop No. 1 to that point.

13. First rap song by a female artist to hit No. 1: Lauryn Hill’s “Doo Wop (That Thing!)” (11/14/98)

While hit singles by groundbreaking MCs Queen Latifah, Salt-n-Pepa, MC Lyte, Lil Kim, Missy Elliott and more all made inroads on the Hot 100 prior to 1998, no female rapper topped the chart before Fugees star Lauryn Hill did so with her breakout solo single “Doo Wop (That Thing!)” The song debuted atop the chart and lasted two weeks on top. It was the only single by a female rapper without any other credited artists to hit No. 1 until Cardi B’s “Bodak Yellow (Money Moves)” 19 years later.

14. First rap artist to replace themselves at No. 1: Ja Rule (Ja Rule feat. Ashanti, “Always on Time” –> Jennifer Lopez feat. Ja Rule, “Ain’t It Funny,” 3/9/02)

By the early ’00s, Ja Rule had earned himself a comfortable role as a go-to duet partner for male-female pop-rap collabs, scoring a number of major hits alongside the likes of Jennifer Lopez, Ashanti and Christina Milian. Two of those became back-to-back No. 1s in early 2002, as Ja’s Ashanti-featuring “Always on Time” was succeeded atop the Hot 100 by his J. Lo team-up “Ain’t It Funny,” making the rapper born Jeffrey Atkins the first MC to replace himself at No. 1.

15. First rap artist to be Billboard‘s year-end Hot 100 artist of the year: Drake (2016)

While it might seem strange for the first rapper to top Billboard‘s year-end Hot 100 artist listing to come 21 years after the first rap song to top the year-end Hot 100, it’s worth noting that the artist chart was introduced by Billboard in 2006, so it’s entirely possible that a rap artist would have topped it earlier had it been around. Nonetheless, it still took a decade — unless you count Jamaican dancehall MC Sean Paul, who topped the inaugural listing in 2006 — for a rapper to take the chart’s top honors, until Drake’s dominant 2016, where he scored No. 1s both as a featured artist on Rihanna’s “Work” and (for the first time) as a lead artist on the 10-week leader “One Dance.”