1. “The Sweetest Thing” – Lauryn Hill
“The Sweetest Thing” steers clear of the dramatic fireworks of some of the other love songs on this list in favor of subtle nuance. Lauryn captures love’s mundane comforts and playfully laments some of the trivial stumbling blocks, too. Ever the poet, L. Boogie delicately serenades her “Sweet prince of the ghetto. Your kisses taste like amaretto.” That said, I have to admit that my favorite line comes toward the end when she wails “I sometimes watch you in your sleep.” It sounds beautiful in the song but on paper it’s hilariously creepy.
2. “Love Of My Life” – Erykah Badu ft. Common
This is probably the most unorthodox song in the group with its fusion of experimental neo-soul sounds. There’s even an eerie arrangement of Rhodes electronic piano notes evoking a SciFi or horror film score. But then in comes the flute to brighten the mood. And although the lyrics are loaded with metaphors that personify the hip hop genre, the references seamlessly apply to interpersonal relationships as well. Of course Badu saves the best for last—belting out the final lyrics with painfully uninhibited raw emotion until the song fades to silence.
3. “Angel of Mine” – Monica
This chart-topping love song landed at #62 on Billboard’s U.S. Hot 100 list for the 90’s. It was actually a cover of a song released by a British R&B group Eternal just a year before Monica took a stab at it and made it her own. Monica’s deep voice has a rich earthy texture with a hint of androgyny at times. The lyrics are sweet and simple, making it a bona-fide 90’s classic.
4. “All My Life” – K-Ci & JoJo
Now this is a power ballad of Celine Dion proportions! JoJo actually originally wrote the lyrics with his daughter in mind as inspiration, and the tune still has a universal quality about it, applicable to all genres of love. The vocals of this Grammy-nominated hit are so powerful that singing it requires nothing less than the strength and stamina of an athlete.
5. “Happily Ever After” – Case
This is probably the least well-known song on the list. I suspect the music video cameo by a young, pre-icon status Beyoncé as the main love interest helped sucker me in. But the lyrics explicitly reminisce about a man’s successful marriage proposal to the love of his life. Case joyfully croons his appreciation and admiration for his soulmate and basks in the brightness of their future together. It’s a winner.
6. “Spend My Life With You” – Eric Benet ft. Tamia
While also not a huge commercial success, “Spend My Life With You” did get nominated for a Grammy and has shown longevity as being a popular choice among amateur singers doing adorable long-distance webcam duets for YouTube (including the one below). Benet’s falsetto is irresistible and Tamia adds the perfect complement—I just love the way she goes off-roading during the chorus.
7. “Have You Ever” – Brandy
This song was written and produced by music industry heavyweights Diane Warren and David Foster. While the lyrics tell a story of longing, there’s an implicit light at the end of the tunnel. You expect everything to work out in the end. Brandy’s youthful voice is fragile and vulnerable, but she hits those power-ballad high notes with passion and determination.
8. “Can’t Take My Eyes Off of You” – Lauryn Hill
Lauryn Hill’s cover of “Can’t Take My Eyes Off of You” infuses a creative array of hip hop elements into Frankie Valli’s 1967 classic. The lyrics recount a head-over-heels infatuation and they are sung as if being shouted from a rooftop. In transitioning from verse to chorus, Hill’s vocals seamlessly swell from soft and coy to soaring and jubilant. And oh how we savor those throwback background harmonies.
9. “Breathe Again” – Toni Braxton
This is more of a “contemporary adult” R&B song. In other words, it has a slight “elevator music at Macy’s” feel to it. It’s the oldest song on the list. Braxton’s iconic, husky contralto voice actually tells the story of a love that seems to be unraveling. But the lyrics convey such an immense amount of devotion from the singer, I was willing to bend my rules a little. Plus, she’s wearing a fucking wedding dress in the video for crying out loud.
10 “21 Questions” – 50 Cent ft. Nate Dogg
Rapper 50 Cent reveals his romantic side in his hit song “21 Questions.” Producer Dirty Swift sampled elements of the great Barry White’s “It’s Only Love Doing Its Thing” to create the cut’s backbone: a bittersweet guitar riff (which you can learn by following the YouTube tutorial below!). The aptly titled track features 50 gently reciting a list of questions to his significant other that range from cute and mellow to sobering, starting with “If I fell off tomorrow would you still love me?” Brownie points for casting one of my girl crushes Meagan Good as the main love interest in the video.