The 1990s was a time of countless musical eras. With singers like Madonna and Whitney Houston bringing pop into the new era and rappers like Dr. Dre and Ice Cube doing their thing, the decade morphed into much more.

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Rock, rap, grunge, alternative, bubblegum pop, boy bands, girl groups and more. It is enough to make one’s musical mind spin. Here are nine songs that defined the 1990s.

1. “Smells Like Teen Spirit,” Nirvana (1991)

It’s not the song that started the grunge movement, but it’s the one that crystalized its importance and its reach. Nirvana was the biggest band in the world after the release of its 1991 album, Nevermind. And while frontman Kurt Cobain died just a few years later, his memory lives on thanks to songs like “Smells Like Teen Spirit,” which boasts more than 1.5 billion YouTube views.

2. “…Baby One More Time,” Britney Spears (1998)

Post-Cobain, popular music veered away from the dark, brooding nature of grunge into the bright and sticky styles of pop. Enter Britney Spears. Her music video for “…Baby One More Time,” from the album of the same name, is essential ’90s watching.

3. “Wannabe,” Spice Girls (1996)

We go from solo girl pop to the group variety. This 1996 song, which came out a few years before Spears, is the quintessential song about friendship. It’s also supremely catchy.

4. “Nuthin’ but a ‘G’ Thang,” Dr. Dre feat. Snoop Doggy Dogg (1992)

Dr. Dre’s 1992 album, The Chronic announced him as a solo artist, separate from N.W.A. It also announced the arrival of newcomer Snoop Dogg, whom Dre discovered.

5. “Ironic,” Alanis Morissette (1995)

It’s like raaaaaaiiiiinnnn on your wedddiiiinnngg daaay! The chorus of this song still rings in the ears of music fans. Truly, Morissette’s 1995 album, Jagged Little Pill might be the record of the ’90s. It bridged rock with pop with alternative. Even had harmonica!

6. “Juicy,” The Notorious B.I.G (1994)

The perils of list making, this list should easily also have Tupac on it. But we’ll take the chance here, as we talk about the artful and skilled rapper whom Pac feuded with, Biggie, to also bring up his name. Sadly, the West Coast-East Coast rap war of the decade claimed both their lives. But the silver lining is that their music subsists, in all of its sublime lyricism. Case in point: “Juicy.”

7. “Wonderwall,” Oasis (1995)

The Gallagher brothers. Either writing hit songs or fighting. They’re worse than the Succession siblings. They, too, boast a number of hits, perhaps no bigger than the acoustic-driven “Wonderwall.”

8. “Losing My Religion,” R.E.M. (1991)

A timeless song, an artful video. But the reason this track is on the list is to honor R.E.M., which in many ways kicked off the college radio and alternative rock revolutions of the era.

9. “1979,” Smashing Pumpkins (1996)

Smashing Pumpkins, for all their oddities, was one of the biggest bands of the decade. There’s no debating that. And while we could have Pearl Jam, Soundgarden, TLC or any other band, we’ll end here with Billy Corgan and his hit, “1979.”

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