1. "Un-Break My Heart" — Toni Braxton
2. "Pony" — Ginuwine
Sorry, but Ginuwine's mastery of sexual innuendo and the double entrendre should make the rest of us want to give up flirting forever. This was his debut single and I think we can all agree that he's been cashing the musical and sensual checks since he starting writing back in 1996.
3. "1979" — Smashing Pumpkins
"1979" was the second single from The Smashing Pumpkins' big old third studio album (a double disc called Mellon Collie and the Infinite Sadness). Less angsty, more synth-y, and way more — GASP — sweet and poppy than was typical for Smashing Pumpkins, this single won the MTV Video Music Award for Best Alternative Video in 1996.
4. "Criminal" — Fiona Apple
Fiona Apple's debut album was called Tidal and this was its third released single. (The single itself was released in 1997, but the album is from 1996.) Apple said that "Criminal" is about "feeling bad for getting something so easily by using your sexuality."
5. "Killing Me Softly" — Fugees
6. "What I Got" — Sublime
This was the first single to be released from the third album by California poppy ska band Sublime. By the time it was released, Sublime's lead singer Bradley Nowell had died of a heroin overdose.
7. "Say You'll Be There" — Spice Girls
What are you going to do, not sing along this? "Wannabe" was probably the first Spice Girls song you ever heard and this one is the second. It's from their debut album, and in the video the Spice Girls are Charlie's Angels-esque action heroes. In a desert. Dancing.
8. "Woo Hah!! Got You All in Check" — Busta Rhymes
Busta Rhymes' mainstream breakout moment was probably his verse on A Tribe Called Quest's single "Scenario" and his appearance in the song's video. Four years later, Busta Rhymes' debut solo album came out with "Woo Hah!!" as the first single. The video is great, too, and was directed by, NBD, Hype Williams.
9. "If It Makes You Happy" — Sheryl Crow
This was the first single from Sheryl Crow's second album. It won Best Female Rock Vocal Performance at the 1997 Grammys. It's kinda confrontational, kinda pretty, and also kinda screamy. Great combo.
10. "Novocaine for the Soul" — Eels
The Eels' first album was called Beautiful Freak and this was its debut single. The lyrics are playful, yet full of existential dread*, the singer has a gravelly voice, there's a Beatles sample, and several times the song pauses and all you hear is the twinkling of what might be is a xylophone. So, in short, a perfectly eclectic and moody mid-'90s alternative rock song.
*"Life is hard
And so am I
You'd better give me something
So I don't die
Novocaine for the soul
Before I sputter out"
11. "Where It's At" — Beck
Odelay was Beck's fourth but highest-selling album and "Where It's At" was the first single released from it. It has plenty of noisey distortion sounds and voiceovers and also a repeated line — "Two turntables and a microphone" — that will haunt us all for life.
12. "Give Me One Reason" — Tracy Chapman
The bluesiest, rockingest ultimatum ever! Chapman's album New Beginning was released in 1995, but this song wasn't released as a single till 1996. It won the 1997 Grammy Award for Best Rock Song. As a bonus you can totally feel free to go ahead and read the lyrics from beginning to end to any significant other who's not holding up their end of the bargain.
13. "If I Ruled the World (Imagine That)" — Nas featuring Lauryn Hill
14. "No Diggity" — Blackstreet
"No Diggity" was a track on Blackstreet's second album. It featured guests verses by Dr. Dre and Queen Pen and spent 31 weeks on Billboard's Hot 100 and won a Grammy in 1998 for for Best R&B Performance. Sorry to anyone who didn't grow up with this song in extremely heavy rotation while you were growing up; your adolescence was meaningless, and your life, by definition, can never great.
15. "Don't Speak" — No Doubt
"Don't Speak" is the saddest breakup song a ska pop band ever recorded and it was the third single from their album Tragic Kingdom.
16. "Lovefool" — The Cardigans
Even if you didn't come of age in the American suburbs in the '90s, you might still be able to imagine how your teenage world would've changed if Leonardo DiCaprio and Claire Danes co-starred in a fast-paced modern-day adaptation of Romeo and Juliet right smack-dab in the middle of your puberty. The song "Lovefool" by the Swedish band The Cardigans was part of the movie's soundtrack and was the band's first international hit.
17. "Tha Crossroads" — Bone-Thugs-n-Harmony
NBD, just a hit song that meditates on not wanting to die, losing people you love, missing them, and hoping to see them again. The song was on their 1996 album E 1999 Eternal. It won a Grammy and was dedicated to Eazy-E, who had recently signed Bone Thugs to his label Ruthless Records. No, you're crying.
18. "Elevators (Me & You)" — OutKast
This is the first single from OutKast's legendary second album ATLiens, released when Big Boi and André 3000 were just 21 years old. Billboard chart-wise, this song was only out-perfomed by later hits "Ms. Jackson" from Stankonia and "Roses" and "Hey Ya," from Speakerboxxx/The Love Below.
19. "Champagne Supernova" — Oasis
The Gallagher brothers made some super-sweet and melancholy music for some two fairly aggro dudes. "Champagne Supernova" was on Oasis's 1995 album (What's the Story) Morning Glory? but was released as a single in 1996. What the hell is the song about? When a music writer asked singer and guitarist Noel Gallagher about the lyrics, calling them ridiculous, he said, "I don’t fucking know." Fair enough, Noel. Fair enough.
20. "Quit Playing Games (With My Heart)" by Backstreet Boys
I'd might personally dispute that this song deserves to be alongside "Un-break My Heart," "No Diggity," and "Criminal," but we can't ignore Backstreet Boys' Top 40 domination in the 1990s, and since this was their debut single in the U.S., well, why not? If Wikipedia is to be believed, the video was filmed at a middle school in Orlando and "The boys dance in the rain, some of them have their shirts unbuttoned in the later half of the music video." Whether or not it's the gayest music video of all time, that's for you to decide.