Drake’s 10 Most Confessional Songs, Ranked

Five albums later, Drake still manages to bring the feels.
July 12, 2018
12 mins read

As Drake acknowledged in the editor’s notes of his fifth studio album, “Scorpion,” fans’ expectations and criticisms have often haunted his longevity in the rap game. “I hate when Drake raps,” “Drake sings too much” or “I like Drake’s older stuff,” listeners have asserted between releases.

However, despite the many dimensions and sounds that drew people to the Canadian rapper, his display of emotion proves to be the commonality that largely contributed to his success. Since the release of his 2009 mixtape, “So Far Gone,” Drake has created a seamless blend between rap and R&B, smooth like rum and coke, creating a shift in contemporary hip-hop.

At the center of a male-dominated industry, Drake has certainly faced his fair share of scrutiny (and memes) for being overly sensitive, but he refuses to run from his feelings. “I know that showin’ emotion don’t ever mean I’m a pussy,” he rapped in the song “Lord Knows” on his 2011 album, “Take Care.”

With new music on the airwaves, now is the perfect time to ask: What are some of Drake’s most personal tracks throughout his career?

So, without further ado, here is my compiled list of the top 10 Drake personal songs.

10. “Under Ground Kings”

Drake briefly elaborates on the complexities of his love life in “Under Ground Kings,” which allows him to boast about his own crown and pay respect to Pimp C, the deceased rapper who’s most known as a founding member of Underground Kingz (UGK).

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Showcasing his eclectic tastes, he teases that depending on the day, he needs a pole dance, romance or a stripper that doesn’t dance. In the second verse, he also offers insight into the decisions that led him to this point. Admiring guys rockin’ grillz and furs, Drake questions, “So why am I in class if this is who I’m trying to be like / So I drop out, lessons I was taught are quick to fade / As soon I realize that turning papers in won’t get me paid.”

Warning, for those of you considering this route, your student loan payments will still be due, and Drizzy can’t help.

9. “Redemption”

For some inexplicable reason, I avoided “Views” when the album first dropped in 2016. I didn’t listen to all of the tracks until a few months ago, which is when I discovered “Redemption.” Once again, Drake uses an ex for inspiration, begging her to be patient as he searches for the right words to apologize.

By the fourth verse, he references multiple failed relationships and friendships, stating, “Not havin’ closure, it take a lot out of me / This year for Christmas I just want apologies.” Ultimately, Drake is ready to forgive, resolve longstanding issues and make up for his mistakes. Unfortunately, second chances or clean slates don’t come that easily — even for the rich and famous.

8. “You & The 6”

Everyone has a soft spot for their mama, and I’m a sucker for Drake’s tribute to his mother, Sandi, on “You & The 6.”

In the first verse, Drake revealed that he hadn’t been returning his mother’s texts, so she relied on mobile Google alerts for information — pretty impressive, considering most middle-aged people struggle to control their ringtone.

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Drake admitted that his life was a mess when he wrote the song, but as always, conversations with his mother helped him overcome the challenges. He said, “At least I always, at least I always see it through / At least I’m always being true to what you taught me / Retired teacher, but your words still got me evolving,” supporting the following refrain, “You and the six raised me right, that shit saved my life.”

7. “Is There More”

At the zenith of his career, Drake begins to search for a greater purpose on “Is There More.”

“Is there more to life than all of these corporate ties / And all of these fortunate times / And all of these asses that never come in proportionate size / Am I missin’ something that’s more important to find? / Like healin’ my soul, like family time / Is there more to life than just when I’m feelin’ alive?” he spitted toward the end of the second verse.

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Considering Drake is a father now, it’s natural for him to reject life’s superficialities and look for a deeper fulfillment. He’s in a period of reflection, sharing the questions that only he can answer, with his fans.

6. “From Time”

The piano harmonies accompanied with Jhene Aiko’s sultry and enigmatic voice makes “From Time” one of the best songs from Drake’s 2013 album, “Nothing Was the Same.” Never abandoning his lost love as a muse, the rapper has a conversation with an old flame.

Drake calls in Sandi for another assist and confessed, “My mother is 66 and her favorite line to hit me with is / Who the fuck wants to be 70 and alone? / You don’t even know what you want from love anymore / I search for something I’m missing and disappear when I’m bored.”

So, maybe his heartbroken ballads aren’t a gimmick after all. Drake is a walking puzzle trying to temper the sting of loneliness.

5. “Hate Sleeping Alone”

A bonus track on “Take Care,”Hate Sleeping Alone” proves that rappers need teddy bears too.

Longtime Drake fans can surmise that the rapper’s lifestyle complicates his relationships. On the track, he raps about a woman that would’ve moved in by now if they weren’t forced to take it slow. In a silky chorus, Drake sings, “I’d rather be with you, but you are not around / So I’ma call somebody up and see if they be down / ‘Cause I hate sleeping alone, I hate sleeping alone.”

Drake’s “somebody” includes random women who are merely alternatives, bed-mates and placeholders because the one who has his heart wants him to give more than he can offer right now. “Hotel to hotel, girl—I could use your company / Full name and birthday, I book a flight, you come to me / But she don’t want a weekend—she wants all of me or none of me / If she can’t work with all of me then she say she done with me,” he rapped.

4. “The Resistance”

As the third song from his debut album, “Thank Me Later,”The Resistance” explores some of the changes Drake has to confront now that his career is on the rise.

He grapples with the internal battle of the fear of fame and an insatiable hunger for success. “What am I afraid of? / This is supposed to be what dreams are made of / But people I don’t have the time to hang with / Always look at me and say the same shit / They say ‘You promised me you would never change,'” he rapped in a guilt-ridden hook that floats over moody synthesizers and subtle arrangements.

Drake continued to dissect his thoughts and feelings bar by bar, reflecting on his failure to keep in touch with his grandmother, a sexual encounter that led to an abortion and a stick-up that took over his old personality and caused him to treat his friends differently.

3. “Emotionless”

Drake’s beef with Pusha T temporarily overshadowed the upcoming release of “Scorpion,” especially when Pusha claimed that Drake had a secret son on “The Story of Adidon.” Fans anticipated either some revenge against his rival rapper or confirmation that the rapper indeed has an heir.

On “Emotionless,” Drake raps about strangers’ opinions and people’s incessant need to impress others, even if it means wearing a mask. Then he gives listeners what they were waiting for: “Look at the way we live / I wasn’t hiding my kid from the world / I was hidin’ the world from my kid / From empty souls who just wake up and look to debate.”

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While some may argue that his contemplative approach to acknowledging the existence of his child was crisis management — or just cheap justification for a well-hidden secret — it’s hard to deny that Drake’s lyrics resonated with a generation that knows the cruelty of social media and blogs all too well.

2. “March 14”

Drake uses “March 14,” the last song on “Scorpion,” to further discuss his feelings about his son, which manages to unveil a new level of emotional depth in his material.

He addresses his relationship he has with the child’s mother and even celebrates the DNA test results. However, the most poignant lyrics include: “Single father, I hate when I hear it / I used to challenge my parents on every album / Now I’m embarrassed to tell ’em I ended up as a co-parent / Always promised the family unit / I wanted it to be different because I’ve been through it / But this is the harsh truth now / And fairy tales are saved for the bedtime stories I tell you now.”

Daddy Drake has been formally introduced to the world, and with a new responsibility to raise an extension of himself to be an honest and responsible man comes emotions that blaze higher than any former flame.

1. “Look What You’ve Done”

Look What You’ve Done” is easily of my favorite Drake songs. The rapper is stripped down to his core, and listeners receive a dose of Aubrey Drake Graham in full force as he pays tribute to his mother, grandmother and uncle. Furthermore, the piano melody, heartbeat bounce and percussion loop nearly transform the track into an OVO graduation speech, which is sure to hit you right in the feels.

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In the first verse, Drake recalls an argument where his mother accused him of being just like his father, an obvious trigger for the man whose father walked out on him. After detailing the heated exchange, he returns to the tenderness of their relationship and sang, “You love me and I love you / And your heart hurts, mine does too / And it’s just words and they cut deep / But it’s our world, it’s just us two / I see painkillers on the kitchen counter / I hate to see it all hurt so bad / But maybe I wouldn’t have worked this hard / If you were healthy and it weren’t so bad.”

You can instantly feel the struggle of a single mother, and a son who wants to do right by her. However, the last few lines are a ray of sunlight. After mentioning the success of “So Far Gone,” Drake proudly rapped, “You get the operation you dreamed of / And I finally send you to Rome / I get to make good on my promise / It all worked out, girl, we shoulda known / Cause you deserve it.”

Drake proceeds to honor his Uncle Steve, who welcomed him into his home, consistently encouraged his dreams and supported him financially. Lastly, the song ends with a voicemail from his grandmother, Evelyn, who remembers the good times they shared and thanks him for keeping her in a comfortable facility. Her voice is weakened by age, but strengthened with emotion, sending listeners’ tears (okay maybe just mine) down a waterslide to the repeat button.

Ayanna Totten, East Stroudsburg University

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Ayanna Totten

East Stroudsburg University

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