For many fans of rap, the 90s were a time of untold heights. The genre was beginning to diversify in many directions—all without early MCs losing their originality. It was also the period when the East Coast-West Coast rivalry took off, coupled with major industry changes that shook up the music world.

Toss in plenty of technical advances and it’s a period that any rap fan could sink a few hours into studying. But which tracks, specifically, are worth taking a closer look at? Let’s list off some of the most iconic and best songs from the 1990s.

It Was a Good Day (Ice Cube, 1992)

To date, this hit remains Ice Cube’s biggest hit—one that Rolling Stone listed as No. 36 of their 100 Greatest Songs of the 90s (note that includes every genre of music). This should come as no surprise, as this song is has the smooth and lyrical energy of West Coast hits coupled with Ice Cube’s impeccable flow.

The lyrics call back to all types of daily activities. There’s even a mention of craps, a popular casino game. At the time of the song’s release, it would have been played at physical establishments. Today, fans of casino games (craps and beyond) are used to playing online and they can find an up-to-date list here of the best casinos available on the internet and their best offers. In fact, ‘It Was a Good Day’ is one of many songs that reference the popularity of casino games. Other hits from the hip-hop world include Kendrick Lamar’s ‘Vegas’ and Jay-Z and Kanye West’s song ‘Who Gon Stop Me’.

C.R.E.A.M. (Wu-Tang Clan, 1993)

Worldwide, many music fans would recognize the piana sample from this song. C.R.E.A.M. was the final release on the rap group’s debut album, putting them on the map across the US and far beyond. Unlike Ice Cube’s hit, which focused on a life in the day, this song takes a tougher look at life in the streets of New York City.

Oddly enough, this song wasn’t an immediate hit upon its release. It didn’t hit major commercial success, nor was it considered the main hit on the album, Enter the Wu-Tang. But over the year, the song continued to gain attention from critics and fans, eventually becoming one of the best hip-hop tracks of all time.

Mathematics (Mos Def, 1999)

Like the other names on this list, Mos Def has taken a strong career in the 90s and turned it into a lifelong legacy. He’s known for his lyrical ability to paint a picture—one that very quickly began revolving around social justice causes. Based in Brooklyn, New York, Mos Def became one of the biggest names in the East Coast scene.

His hit Mathematics from the eponymous album is based on the idea that it takes a mathematical and statistical mind to understand the complexities of the world. At one point, he even raps some stats in numerical order. The original release actually included samples from other artists, including Erykah Badu, Fat Joe, and James Brown.

Passin’ Me By (The Pharcyde, 1992)

We’re rounding off this list with one of the more unique 90s hits that not as many modern rap fans might know. In 1992, West Coast group The Pharcyde decided to explore their reality through a different lens. Rather than take a more hardened view of a difficult life, the song explores things like romance and entertainment through a comedic and cheeky lens.

All four MCs recount some of their more boyish crushes from back in the day, recounting stories of young love that goes awry with a catchy saxophone riff in the background. It has remained an influential underground hit, which has seen more attention in recent years. Since its release, it’s been sampled in a handful of movies and film projects, from Atlanta to Last Chance U: Basketball.