The act of creating a mixtape has such a romantic connection to music, and not just when the tape itself is an attempt to woo someone (though it's certainly always been a labor of love). The practice began in the '70s and '80s with cassettes and careful recording of songs from vinyl records, radio broadcasts, or other cassettes, and eventually began getting easier in the '90s with the rise of the compact disc (CD) and eventually CD "burning" technology. Nowadays, all that energy has been translated into the likes of Spotify or Apple Music playlists, though the thought behind mixtapes still remains.

The rise of CDs certainly came at an interesting time during the '90s. There was the early decade's rise of grunge music, of course, as well as the latter end's transition into pop purveyors and boy bands, with curious one-hit wonders and singer-songwriter endeavors in between. While this era of pop culture might not receive as much attention as other periods, the music has a certain, underrated charm that continues to have lasting appeal many years later.

1 Soul Asylum, Runaway Train (1992)

Rolling Wheels Of Feeling

Minnesota-based rockers Soul Asylum introduced the biggest hit of their career, "Runaway Train," as a single off their 1992 album, Grave Dancers Union. Written by lead singer Dave Pirner about his experiences dealing with depression, the track's success wound up leading to a Grammy Award for the group, Grave Dancers Union going multi-platinum in sales, and a famous music video featuring images of missing people.

Despite the growing popularity of the sound and style of the growing '90s grunge era at the time, "Runaway Train" flew in the face of this convention with its mid-tempo acoustic-led balladry. While some might have found the style a bit on the syrupy side, there's still a lasting endearment to "Runaway Train" that hasn't abated since it debuted. That even amid all the flannel and ripped jeans, there was still room to get sad and honest behind the long hair in your eyes.

2 NSYNC, I Want You Back (1997)

Figures Of The Boy Band Blitz

Ah, the '90s nostalgia of songs like "I Want You Back." Released in 1997 off their debut self-titled album, NSYNC was one of the best boy bands to come out of the craze, which began with New Kids on the Block in the late '80s. It then roared with horsepower by the late '90s to include the Backstreet Boys and 98 Degrees. NSYNC was, of course, also the signature launching pad for the future mega-solo career of founding member and vocalist Justin Timberlake.

This era of popularity was certainly not by accident. While some might deny or deride their cultural sway in hindsight, boy band songs like NSYNC's "I Want You Back" are still helplessly catchy, well-sung and harmonized, and wear their emotional lyrical intentions front and center. Add in the seamless dancing and choreography stitched into the material on the live stage, and whether you consider it guilty or not, NSYNC remains a pleasure to this day.

3 Sublime, Santeria (1996)

A Bittersweet Ska Breakthrough

Ska punk band Sublime released their third album, Sublime, just months after lead singer Bradley Nowell tragically died of a heroin overdose. Sadder still, the 1996 record wound up being the band's commercial breakout, even though Sublime couldn't tour behind it and had dissolved by that point due to Nowell's ing. Sublime singles "Santeria" and "What I Got" also ended up being two of the group's signature songs.

Sublime is one of those unusually quirky hallmarks of the '90s that might have seemed strange on paper with their fusion of ska, punk, and Jamaican reggae flow. But "Santeria" just works, in a style somewhere between Mexico and the Red Hot Chili Peppers' spirited takes on California. Not that RH lead singer Anthony Kiedis often mused about "popping a cap" in a guy named "Sancho" for allegedly stealing his girlfriend, but that was just part of what gave Sublime their unusually wry slacker sense of wit for the '90s.

4 Coolio, Gangsta's Paradise (1995)

A Dangerous Mind's Mindset

Rapper Coolio's 1995 song "Gangsta's Paradise" would eclipse Dangerous Minds, the film that introduced the song to the world. The track was so successful that Coolio wound up giving his second studio album (also released in 1995) the same name. "Gangsta's Paradise" sampled the 1976 Stevie Wonder song "Pastime Paradise," and at the request of Wonder, Coolio removed all cursing in the lyrics in order to be able to use the sample.

"Gangsta's Paradise" combines the slick flow of rap with the haunting backdrop of a gospel choir's angelic feeling. The contrast works perfectly between the lyrics for Coolio, who talks about the hard and often violent life of living in the streets against his brewing sadness, wondering if he can continue to survive all the dangers of it. "Gangsta's Paradise" represents a very real scenario for many living close to the bone of life, and the starkly depicted reality is part of what gives the song so much strength.

5 Blues Traveler, Hook (1994)

The Winking Nod Brings You Back

Blues Traveler's song "Hook," much like the aforementioned Sublime and "Santeria," has a certain type of coy, niche-level charm that continues to give the '90s a distinct place in hindsight's musical timeline. Released in 1994 as part of the band's fourth studio album Four, lead man and prolific harmonica player John Popper wrote the smash hit about musical "hooks" designed to ensnare listeners with a catchy framework.

The song essentially boils down to satire, poking fun at the idea of singing just about anything, but doing it with a certain structure and inflection to capture audience attention. "Hook" was mainly intended to take a shot at empty-headed pop songs topping the charts back then, but in a stroke of irony, the humorous earworm of the song itself wound up making it quite popular as well. Turns out it's not just the "Hook" that brings you back, but Blues Traveler as well.

6 TLC, Waterfalls (1994)

Chasing Down Social Commentary

The song "Waterfalls" was released in 1994 by storied R&B/hip-hop trio TLC (made up of Lisa "Left Eye" Lopes, Tionne "T-Boz" Watkins, and Rozonda "Chili" Thomas) as the third single off of their second studio album CrazySexyCool. Considered one of the group's most iconic songs, "Waterfalls" helped to not only put TLC on the path of musical success, but also helped spread a social message related to the illegal drug trade, the HIV/AIDS epidemic, and the dangers of promiscuity.

And while the trajectory of TLC would permanently change after the death of Lopes in a car crash in 2002, their legacy to the '90s remains as prominent as similar girl groups of the time, including Destiny's Child and Salt N Pepa. Even decades later, TLC still has a grooving smoothness to their sound on "Waterfalls" that isn't dated or confined to the '90s.

7 Goo Goo Dolls, Iris (1998)

A Stunning Soundtrack Statement

Buffalo, NY's own Goo Goo Dolls created one of their biggest, and most mixtape-worthy, hits in 1998, writing "Iris" for the Nicholas Cage-Meg Ryan film entitled City of Angels. "Iris" was also placed on the band's 1998 studio album Dizzy Up the Girl, which went on to become one of the Goo Goo Dolls most commercially successful LPs.

Just listening to "Iris" feels like embracing a love story that's undeniably powerful, especially to anyone who's ever felt the thunderstrike sensation of the romance and attraction that can come from finding what feels like that significant other in your life. Just hearing lines like "and I'd give up forever to touch you" and "you're the closest to heaven that I've ever been" feels like the heat behind many a Myspace relationship post back in the day. And the ion of "Iris" still remains.

8 Counting Crows, Mr. Jones (1993)

Aspiration For The Big Lights

"Mr. Jones" was the lead single from the Counting Crows' 1993 debut album August and Everything After. It not only served as the album's first single, but became a significant radio hit and is often credited as giving Counting Crows their breakout start. The lyrics describe two struggling musicians aspiring to become popular and thinking that finding fame and the spotlight might cover up some of their overall worries and loneliness in life.

Despite those heavier thoughts, "Mr. Jones" also thrives because it covers over the emotional gray areas with a fun and carefree rock-and-roll exterior that makes for a perfect fit into almost any summer-themed playlist. "Mr. Jones" feels a lot like the youthful aspiration to be more in life while wanting to be carefree and driven by ion. The time for self-reflection and worry will come later, because right now it's all gas and no brakes.

9 Nirvana, Smells Like Teen Spirit (1991)

The Anthem Within A Feeling

While lyrical interpretations of the meaning behind Nirvana's "Smells Like Teen Spirit" have widely varied from rallying teen anthem to complete nonsense over the years, there's still something irreparably iconic about the song. Not just because of its place in overall popular music and its role in the sound of Nirvana's best album, 1991's Nevermind, but also because it just sounds like an anthem song built perfectly for the youth of the time and the grunge movement itself.

Between Krist Novoselic's deep, thundering bass tones, Dave Grohl's hammering drum fills, and lead man Kurt Cobain's signature riff work on the guitar and yowling vocal screech, "Smells Like Teen Spirit" just seems to capture the emotional spirit of youth. Not through specific words but in the rise and fall of simple existence. The ionate thrash, the anger, the leveling rise and fall of emotions, "Smells Like Teen Spirit" captures the turbulent, washing machine spiral of growing up.

10 Hootie & The Blowfish, Only Wanna Be With You (1994)

A Rock Band's '90s Dietary Staple

Long before his successful solo turn as a country music artist, singer-songwriter Darius Rucker was turning heads on the charts during his tenure as lead man of the rock group Hootie & The Blowfish. The debut album Cracked Rear View, released in 1994, became one of the best-selling records in the history of the United States, propelled by multiple singles including "Hold My Hand" and "Only Wanna Be With You."

While some have critiqued songs like "Only Wanna Be With You" as pudding-level soft-rock when looking back on the '90s, there's a certain warmth of nostalgia in its romantic pop-rock-leaning roots. Much like Counting Crows and "Mr. Jones," there's less concern about life's worries and more time spent just living comfortably in the story of the music. This is relaxed-fit around the campfire type of fun, a sort of Jimmy Buffett way of looking back at the decade. Good for any comforting '90s playlist.