Sad Songs of R&B: 20 Tunes to Satisfy the Winter Blues

Baby, it's cold outside. Well, OK, it's getting there and before we know it winter will be upon us. Sure, people like to romanticize about the indoor activities that go on during the cold weather (Google "cuffing season"), but let's face the fact that winter is a gloomy season. The trees lose their leaves and all of nature dies; it's actually quite depressing when you think about it. Throw in those extra five or 10 pounds you gain from the holidays or emotional eating and before you know it, your body is soft and your soul is sad.

We won't go too far off the edge, but here at The BoomBox, we feel that the best antidote for the winter blues is a good cry. And we have the perfect soundtrack for the tears courtesy of R&B singers like Brian McKnight, R. Kelly, Lauryn Hill and Mary J. Blige. Here are 20 songs to last you through the winter months, complete with tales of breakups and mourning. Hopefully the sad songs and a sad mood will cancel one another out. Let's see how it works.

20. "Un-Break My Heart," Toni Braxton

The saddest part about this song is fathoming someone like Toni Braxton having to beg a man to love her. Then again, in the video, her ex-boyfriend is Tyson Beckford so you can kind of understand that backwards thinking. Still, Toni wants her heart "un-broken" like that's even possible. Nothing like a male model to mend it though, right?

19. "Anytime," Brian McKnight

Brian McKnight is arguably the king of sad songs. On this one, he's wondering if he crosses his ex-girlfriend's mind "anytime." He misses her and opts to spend his days thinking about her and wondering if she does the same. If that isn't sad, then what is? Perhaps McKnight's retrn to the spotlight earlier this year with a song called "How Your Pussy Works"? That's sad for a whole other reason.

18. "Losing You," Solange

Kudos for Solange for attempting to make her latest song upbeat even though it's pretty upsetting. She's really trying to find the light at the end of the tunnel in the midst of losing the one she loves. And here all along we thought the saddest thing going on in Solange's life was having to dance in her sister Beyonce's shadow. Who knew? Certainly not us.

17. "I Miss You," Aaron Hall

Aaron Hall's wife dies in the video for this song. We learn many years later that there was no deceased wife. He's not even married. So basically he killed a woman in his video that never existed. Let's give him the pass though since he was an integral part of the New Jack Swing Era. This song is still sad as hell though.

16. "Killing Me Softly," The Fugees

Sure, Roberta Flack created this song, but the Fugees brought it back to life thanks to Lauryn Hill's chops. While the interpretation of this song -- created by Hill, Wyclef Jean and Pras -- in the video has really nothing to do with the meaning behind the track, hearing Ms. Hill being "killed softly" is sad enough.

15. "Through With Love,” Destiny’s Child

Imagine if Queen Bey really was through with love after making this song? There would be no Jay-Z and Beyoncé – err Jayonce. There would be no Blue Ivy Carter, no Hip-Hop's Royal Couple. That's the real sad story here: imagining a life where Jay-Z and Beyoncé weren't together.

14. "Gangsta Lean," DRS

Sorta one-hit wonders DRS made quite the sad song back in the '90s, about all their fallen homies. The interesting thing about this song is DRS is singing about driving to heaven in that "gangsta lean" aka sitting low in their ride. Two years later, Adina Howard would sing "Freak Like Me" in 1995, telling the story of driving her beat piece around the hood in a gangsta lean. Not nearly as sentimental when Ms. Howard sang those words.

13. "Marvin's Room (Remix)," JoJo

Yes, Drake took emo to the next level when he released "Marvin's Room." However, JoJo's interpretation of the track makes her sound insane. First she's taking Adderall with Red Bull (big mistake, lady) and then sexting her ex to prove she's having a better time than he is. We're just sayin' you can do better, JoJo. Now put your shirt back on and get back in your house.

12. "All Cried Out," Allure Feat. 112

"Apology not accepted, admit to the broken hearts you collected." Ouch. Those words will forever resonate as the epitome of "a woman scorned" lyrics. While the members of 112 are sorry for doing the girls of Allure dirty (we know they're just acting, guys), the girls are done. They're all cried out. We've all been there, haven't we?

11. "Grenade," Bruno Mars

Bruno Mars loves a woman so much that he'd catch a grenade for her. And no, he doesn't mean the "grenades" that the cast of the "Jersey Shore" would take home on a drunken night. He means the mini-war bombs that maim people. Oh, unrequited love, you really are a weapon of mass destruction.

10. "Don't Leave Me," Blackstreet

"If you take your love away from me, I'll go crazy. I'll go insane." So many songs on this list are about women begging men to still love them. Here we have the men of Blackstreet doing it for a change. Despite the fact that this song found its way to the "Nutty Professor" soundtrack, "Don't Leave Me" is still a really great song centered on pleading.

9. "Wicked Games," The Weeknd

Drugs, sadness, more drugs and sadness. That is the recipe for a typical song by the Weeknd. Hearing this title would suggest that the Toronto crooner cosigned by Drake was on his Chris Isaak and singing about his woman playing some wicked game on him. Oh no. Abel Tesfaye, his government name, is the one playing the wicked game on the woman. What a sad flipping of the script.

8. "I Love You," Mary J. Blige

Mary J. Blige gets left in this song. Then she gets insomnia due to all of the "pretty memories" she has with her man. The track is sob-worthy, as MJB seals each line with, "For the record, I love you." Thank goodness she adds Smif-N-Wessun to the remix to lighten the mood. "I shine, you shine. Shine."

7. "If I Could Turn Back the Hands of Time," R. Kelly

Yet another song where someone dies. R. Kelly does a better job of emoting, though, and in the video he really drives the point home. Then of course the song changes meaning in the film "The Wood" when Omar Epps' character sees Sanaa Lathan's character after years of still being in love and regretting breaking up. This track hits on multiple levels.

6. "Cold Case Love," Rihanna

Rihanna has this knack for always making the end of love sound like murder. It's like her thing. Maybe it's not the best thing to be known for, but damn RiRi is good at it. In a way she's right too. Losing love does involve some degree of death. Only difference is, Rihanna makes it violent. Let's not ask where she gets that from.

5. "Bad Religion," Frank Ocean

It's tough to pick which Frank Ocean song is the saddest when they're all pretty sad. "Bad Religion" wins though with its introspective lyrics about love being a religion or something to believe in -- yada, yada. The runners-up for the Saddest Frank Ocean Song Award would be "Swim Good" and "American Wedding" (off his mixtape, Nostalgia, Ultra) plus anything else found on his debut album, Channel Orange.

4. "Ex-Factor," Lauryn Hill

Now that the cat's out of the bag about Lauryn Hill and Wyclef having an affair -- read the latter's new book Purposeif you're not in the know -- this song has so much more meaning. Nobody wants to hear Hill be sad; it's like the musical equivalent to watching a baby seal get clubbed. On a positive note, she did write one of the best breakup songs in breakup song history. Too bad the story behind it had to be true.

3. "Heartless," Kanye West

Sure, hearing Kanye West sing with Auto-Tune is the most depressing aspect of this song. However, Yeezy lamenting over a heartless woman is something anyone can relate to. One thing is for certain: when Kanye isn't making songs about swag and self-deprecation, he knows how to make a sad song like nobody's business.

2. "I'll Be Missing You," Diddy Feat. Faith Evans

Puffy, as he was called during those '90s glory days, made the greatest memorial on the passing of Notorious B.I.G. He called on the late rapper's wife Faith Evans to take the lyrical journey with him. "I'll Be Missing You" can be about losing any loved one, but Biggie's passing made everyone feel like they lost their favorite hip-hop hero. This song was the best way to describe hip-hop's feelings about losing him.

1. "It's So Hard to Say Goodbye to Yesterday," Boyz II Men

This song was the soundtrack to many a high school graduation. Completely acapella, Boyz II Men snapped their fingers and hummed their way through one of the saddest songs to date. It was in memory of a good friend of theirs (much like Diddy's opus), yet this song could be about any special someone leaving this earth. Replay this one with a box of tissues, everyone.