Drake's 'Care Package': Ranking All The Songs Based on Their Emotional Baggage

Drake
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Drake performs at the New Look Wireless Birthday Party at Finsbury Park on June 28, 2015 in London.

Just when you thought it was safe to reignite your confidence during Hot Girl Summer, in comes Drake swooping in with an overwhelming wave of emotion.

On Friday (Aug. 2), the rapper released Care Package, a compilation of deep cuts that diehard fans once had to fervently rip off sites like Soundcloud, YouTube and Zippyshare as they weren’t readily accessible on major streaming services. But as he did with his So Far Gone mixtape for its 10th anniversary earlier this year, Drake acknowledged the power of streaming, packaging his most beloved loosies into one convenient album.

Many of the tracks on Care Package spark key moments in not only Drake’s personal life, but the lives of fans that found solace in his tear-stricken lyrics and signature languid melodies. From “I Get Lonely” to “Days in the East” and “How Bout Now,” these songs will remind you of the first girl who broke your heart, that guy you met in the club’s VIP section that ghosted you and all the late nights you drunkenly cried on the phone to your ex.

So while you reach for the nearest Kleenex and a bottle of Merlot, Billboard ranked every song on the album -- based on how deep they take you down the rabbit hole of self-pity.

17. “4pm in Calabasas”

Drake may carry the most feelings than any rapper of his generation, but he does know how to turn into the coldest lyrical assassin, too. This 2016 cut is a jab at one of the many rappers who continuously came for the 6 God: Diddy.

Most Woeful Lyric: “Pistol by my bed, I'm sleep, but I'm awake / For that one night when n---as try reach inside my safe”

16. “Draft Day”

Following the success of 2013’s Nothing Was The Same, Drake was feeling like The Man. He detailed his takeover on 2014’s “Draft Day,” which is more boastful than a somber reflection on his career.

Most Woeful Lyric: “Sometimes I laugh with God about how you can't stop me / I'm his darkest angel probably but he still got me”

15. “Jodeci Freestyle” feat. J. Cole

Leave it to Drake to spit braggadocious lyrics on a song that simultaneously pays homage to Jodeci. He and J. Cole compare themselves to the iconic ‘90s R&B group as they happily look back on all the girls they’ve stolen from their enemies.

Most Woeful Lyric: “Caught fire just to have n---as ignore me and my flame / 'Bout to burn down the house, they tryna put me in the rain, no”

14. “5 AM in Toronto”

Released as a teaser track ahead of Nothing Was the Same, “5 AM in Toronto” finds Drake less forlorn and more skeptical about the people he surrounds himself with. He rambles on about how friends who he thought he could trust become fake as he continues to shine in the spotlight. And of course, he sneaks a few subliminals in there, predicting his future GOAT status.

Most Woeful Lyric: “'Cause I show love, never get the same outta n----s / Guess it's funny how money can make change outta n----s”

13. “Free Spirit” feat. Rick Ross

Ahead of 2011’s Take Care, Drake dropped a handful of tunes that reminded you that he’s indeed the shit. “Free Spirit” is a notable highlight, as he and frequent collaborator Rick Ross brag about the latest lady friend they snuck in their respective beds. Still no word on where these ladies tatted the rappers’ names, though.

Most Woeful Lyric: “These days keep going by too fast, so give me anything to make shit go slow”

12. “Dreams Money Can Buy”

Drake showed us early on his ability to show off how much better he is compared to his predecessors… while also searching to find true love in the hearts of broken women. It’s truly a gift how he manages to combine two opposing themes on a singular track, but that’s why we’ve stanned all these years.

Most Woeful Lyric: “I want women to cry and pour out they heart for me / And tell me how much they hate it when they apart from me”

11. “How Bout Now”

2014’s “How Bout Now,” which showed up on If You’re Reading This, It’s Too Late a year later, is the ultimate middle finger to any girl whoever doubted you before your glow up. This vengeful track still remains an inspiration for those Instagram captions dedicated to ex-flames.

Most Woeful Lyric: “Remember I deleted all my other girls' numbers out the phone for you? / Remember when you had to take the bar exam, I drove in the snow for you?”

10. “Trust Issues”

Deploying his hook used on DJ Khaled’s “I’m On One,” Drake spins the original club track into a murky late-night romp when the drinks hit a little too hard. As his sight becomes fuzzier with each sip, the rapper begins to question who’s really down to ride for him.

Most Woeful Lyric: “Tell me, how the fuck we 'posed to stay friends / When you got a bunch of feelings that you don't show?”

9. “Paris Morton Music”

This 2010 cut is another example of Drake sampling himself, as he expands on his “Aston Martin Music” feature for this dedication to model Paris Morton. It’s a reminder to the women he left behind that he will always return to them, no matter how big he gets. Sure Jan...

Most Woeful Lyric: “Hope you forgive me, never meant wrong / Tried to be patient but waited too long”

8. “Heat of the Moment”

Drizzy called upon OVO signee PartyNextDoor to provide background vocals for this steamy 2014 tune. Rather than musing about his legacy or chart successes, the rapper instead wants to focus on the special lady that he’s about to romance in his bedroom.

Most Woeful Lyric: “I wish we had met when I was in my teens / Yes Lord, yes Lord, yes Lord / 'Cause these days I only know conditional love”

7. “Club Paradise” 

Drake has a questionable affinity for strip clubs. 2011’s “Club Paradise” is an ode to one of his favorite Toronto spots, and is yet another reminder to his naysayers that he’s never going to forget where he comes from.

Most Woeful Lyric: “Just lie to my ears / Tell me it feel the same, that's all I've been dying to hear”

6. “Girls Love Beyoncé” feat. James Fauntleroy 

Heartbreak Drake really comes through on this 2013 team-up with James Fauntleroy. The rapper laments about all the relationships that have either caused him distress or heartbreak, which is the reason for his trust issues. And the Destiny’s Child “Say My Name” interpolation just drives the emotional dagger deeper.

Most Woeful Lyric: “Feel like my love life is finished / I've been avoiding commitment / That's why I'm in this position”

5. “I Get Lonely”

TLC’s 1999 FanMail song was moody on its own, but somehow Drake managed to push it even further with his 2010 rendition. With the addition of 40’s chilling production, it becomes a soundtrack for those nights when you’re clutching your pillow in hopes that special someone calls you back.

Most Woeful Lyric: “Said I got an email today / Kind of thought that you forgot about me / But I wanna hit you back to say / Just like you, I get lonely”

4. “The Motion”

Sometimes you don’t want to come to terms with the fact that a relationship is truly over, which is what Drake struggles with on this 2013 tune. He can’t rely on friends or his woman, as they both take advantage of his vulnerability. Toss in Sampha’s grieving vocals and it just makes the tears fall even faster.

Most Woeful Lyric: “The girl that I wanna save is like a danger to my health / Try being with somebody that wanna be somebody else”

3. “Can I” feat. Beyoncé

Beyoncé may only provide a few words on this despondent track, but her presence is just enough to create a foil for Drake’s plea to show his woman how much he really cares. The heavy bass within the sparse production feels like a weight crushing your heart as you try to fix a weakening relationship.

Most Woeful Lyric: “Can I tell you what I think my biggest flaw is, baby? / I try to be consistent, but I can't”

2. “Days in the East”

Back in 2014, Drake and Rihanna were still going through the motions of their alleged on-off relationship. And boy, did the rapper feel a way about it (the song samples Rihanna’s “Stay”). He even seeks advice from the wise Erykah Badu on whether or not he should let go or try to mend what’s left. The distress is almost too much to handle.

Most Woeful Lyric: “I'm terrible at invitin' myself, call me over / Those nights when you need someone else, call me over”

1. “My Side”

The If You’re Reading This, It’s Too Late era was peak Sad Boy Aubrey, and he poured out his sorrows on 2015’s “My Side.” You could almost hear the tears fall on the studio’s microphone as he wails about the relationship that’s slipping through his fingers. Word to the wise: don’t play this one whenever you’re feeling lonely. You just might accidentally DM your ex.

Most Woeful Lyric: “I empower girls that don't deserve it / I don't mean to do that shit on purpose”

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