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Top 36 Best Sad Drake Songs of All Time

Music is all about feelings and always has been. It’s all about changing a mood or heightening one, whether sad, depressing, aggressive, or uplifting. I sometimes listen to happy songs when I am sad. But, I mostly prefer to bask in my misery by listening to sadder music. 

The best sad Drake songs of all time are perfect in situations like this. The Canadian rapper’s music might not be known as sad per se. But he has so many looks and vibes that he has something for every mood. 

Drake is usually known for his club bangers and cool experimental rap tracks that offer something a bit different from the norm. But he isn’t one-dimensional. So, let’s take a look at some of the saddest Drake songs of all time to comfort you as and when you need them.

Best Sad Drake Songs of All Time



Top 36 Best Sad Drake Songs of All Time

1 Karaoke

When I am in the mood for relaxation and reflection, “Karaoke” puts me in the perfect headspace. Old-school rap fans sometimes don’t get Drake’s music, and I can understand that. It doesn’t fit neatly in any box or fulfills what rap aficionados believe rap to be. But, I do not care one iota what they think. 

This relaxing joint basks in electronica and a slow and vibrating beat that offers a moody resonance. I always come away from this tune feeling sad but serene in a chilled state.

What I like best about this Drake song is the story… 

If you listen to the lyrics, it’s about relationship troubles, and we can all relate to that. But, from Drake’s perspective, he is spitting facts on what it’s like handling superstardom and a relationship at the same time. Very seldom do the two sit well together. 

The track was released in 2010 from his album, Thank Me Later, which at the time was cementing the artist as a bonafide Pop star.

2 Doing it Wrong

In my opinion, “Doing it Wrong” is one of the best Drake songs, outside of his club bangers, sad or happy vibes aside. 

The super-laid-back vibe explores love in modern society and how we are constantly looking for the wrong thing. This is another track about relationships. Discussing how Drake needs something different from what he is currently getting from the female in this relationship. 

It’s like when you realize that your relationship is over… 

That alone makes the track so sad sounding. And that makes it one of the best sad Drake songs of all time. The song comes from Drake’s second studio album, Take Care, in 2011. It’s a relatable piece of music, which is why the artist has connected with so many music lovers over the past decade. 

It’s the sort of song that makes me want to cry if I am having problems with a girlfriend, so I get it. I would say it’s a soft love ballad with moments of sadness and regret. A song that perfectly mirrors love and life in the modern world.

3 Brand New

“Brand New” takes it back a couple of years to the 2009 album, So Far Gone, which was essentially his third mixtape release. Sad songs are sometimes very difficult to listen to and absorb because they hit so deeply. And this track is just like that. 

I don’t always listen to it… 

That is because it makes me intrinsically sad. So, you have to be in the right mood to enjoy this joint. Anyone who has been dumped in a relationship will relate to it. This heart-breaking track sounds like a man trying to hold onto a relationship that is already over. He doesn’t quite realize it yet, but he is starting to notice how different things are becoming. 

The R&B vocals work well with the laid-back rap verses making this song quite a deep and meaningful track that can move your soul. 

4 Look What You’ve Done

“Look What You’ve Done” is another track from the 2011 Take Care album. It’s easily one of the best sad Drake songs of all time. And it always puts me in a sad, melancholic mood. 

It uses a beautiful piano rhythm with no drum beat for the first minute or so. And, when it does drop in, the tune remains sad and dreamy.

The lyrical content is very introspective…

It delves into Drake’s life, background, struggles, and journey through love, life, and the music industry. Regret seems to be the main point of the tune, and everyone can feel that. 

Anyone who says they do not regret anything in their life is either a narcissist or hasn’t lived very much. The track also talks about his relationship with his beloved grandmother Evelyn and is essentially an ode to her.

5 Lose You

We’ve covered some of Drake’s sad songs from his earlier albums and mixtapes. Now, it’s time to get a bit more modern with “Lose You” from his 2017 More Life album/mixtape. The entire album is a mismatch of musical styles that shows the artistic growth of the famous Canadian rapper. 

It’s a very reflective track… 

The song has Drake thinking about how his music career has gotten in the way of many relationships. And the people he might have lost due to it.

It’s hard not to commiserate with Drake after listening to the lyrics. And it just goes to show that all the fame and money in the world are not always the answer. 

The slow and melodic piano with a slow and relaxing beat makes this a sad song to listen to. But you can take some solace and inspiration from it too. Even Drake questions his decisions in life, so it’s okay for you to do as well. Nobody is perfect. 

6 Redemption

Concerning big years in the music industry, 2016 might very well be the biggest in Drake’s career. When the album, Views, hit the streets, it changed everything for the rapper. Some of Drake’s best songs and club bangers, like “Hotline Bling,” were on this album. 

However, today I am talking about the best sad Drake songs, and “Redemption” is right up there with his saddest. Again, it’s a very introspective and emotional track that you can feel in the depth of your soul when you listen to it.

So, what’s it about?

The lyrics are about a relationship from the past with an older girlfriend taking him down memory lane about his feelings and regrets. But, the silver lining is that Drake turns the negatives of this situation into positives by remembering what was so good about that old relationship. 

We sometimes lose a partner in life and only then realize how much we miss them when they are gone. And that’s pretty sad. 

7 Sooner Than Later

This is another sad Drake song that is very difficult to listen to if you are not in the mood. Even when I am sad and want to bask in it, I can have a tough time listening to “Sooner Than Later.” There’s a lot of pain in his voice, and you can hear it. 

This is another song from his So Far Gone album and is about losing a love that you can’t get back. Drake said that this song was inspired by one of his all-time favorite singers, Larry Graham, who has a track by the same name. 

This is one of my favorite Drake vocals. It might not be rap or Hip-Hop that your father listened to, but it’s more emotional and deeper than most people want to think about. The chorus hook is “You don’t need no one else,” and that should tell you what this track is all about.

8 Jorja Interlude

It’s time to get back to one of Drake’s mixtapes, the 2017 More Life mixtape. “Jorja Interlude” is a collaboration with Jorja Smith, who is a British singer-songwriter. The song is extremely sad and just goes to show how the artist is not scared, to be honest about his feelings in front of other artists. 

This song is mostly a bit too sad for me regarding the lyrical content. But the beat is a bit more uplifting and offers the perfect foil to the lyrics. 

It’s also very nice on the ears…

Largely due to the cool saxophone sounds and synth voices that penetrate the music. As far as uplifting sad songs on this list go, this should probably be higher up. But Drake has made much sadder songs than this joint. 

As far as listening experiences go, this one is very pleasant and was always a favorite of mine. 

9 Teenage Fever

This sad Drake song is about his teenage crush on R&B singer Jennifer Lopez, more commonly known as J-Lo. Drake even goes as far as to sample “If You Had My Love” by Jennifer Lopez. “Teenage Fever” is also from the 2017 More Life Mixtape and is emotional as hell. 

But, to be fair, everyone is emotional in their teenage years. Especially as a young man who is full of hormones and trying to figure out what women and relationships are all about.

Nostalgia for your teenage crushes is a real thing… 

And, in some respects, it can make you feel sad. Some people think this song is about Drake’s relationship switch with Rihanna from J-Lo, and there might be some truth to that. 

In regards to the composition of the music, the beat is laid-back, abstract, and even jazzy in spots. It’s quite a deep and meaningful track with lots of emotional content.

10 Club Paradise

Last but not least, “Club Paradise” is a very reflective and introspective tune. This track didn’t make an official Drake studio album, but that doesn’t bar it from my list. 

It was released on the 2019 Care Package album, which is essentially a collection of Drake songs that didn’t make one of his main albums. It might be a sad track, but it’s not miserable, and it does have some uplifting qualities. 

There is a lot of storytelling going on here…

And Drake pulls from his own life experiences. I like the Care Package album very much. It’s such a unique mismatch of tracks that were from other projects that didn’t quite make it. 

This is one of Drake’s saddest songs. That’s because you can take something positive from it, and it can even make you feel good by the end. It might not be a club banger or commercial classic, but it does have lots of heart and emotion. And that means something to me.

11 That’s How You Feel

12 Jaded

13 Peak

14 Don’t Matter to Me

15 Take Care (feat. Rihanna)

16 Trust Issues

17 Hotline Bling

18 I Get Lonely

19 My Side

20 Feel No Ways

21 Nothings Into Somethings

22 Signs

23 Let’s Call It Off (feat. Peter Bjorn and John)

24 Keep the Family Close

25 Down Hill

26 Shot For me

27 Marvins Room

28 Hate Sleeping Alone

29 I Get Lonely Too

30 The Resistance

31 From Time

32 The Real Her

33 Own It

34 Too Much

35 Find Your Love

36 Do Not Disturb

Looking for More Sad Music?

Well, take a look at our detailed articles on the Best Sad Songs, the Best Songs About Crying, the Best Songs About Depression, the Best Sad Rap Songs, and the Saddest Kanye West Songs for more songs to match your mood.

Also, you need to hear those tunes. So, check out our reviews of the Best Headphones for Hip-Hop, the Most Comfortable Headphones, the Best Headphones for Music, the Best Headphones Under $200, as well as the Best Wireless Bluetooth Headphones that you can buy in 2023.

Best Sad Drake Songs of All Time – Final Thoughts

When we discuss the greatest Drake songs, we usually talk about “Nice For What,” “Child’s Play,” “Portland,” “Know Yourself,” and many more. He has everything in his catalog, from club bangers and massive commercial hits to collaborations and sad songs. 

Drake is a true artist in every sense… 

However, he does get stick from old-school Hip-Hop fans because his tracks are not like rap music as we know it. That’s a fair assessment. Drake is Drake, and he doesn’t have to be pigeonholed into one musical genre, in my opinion.

The truth is that Drake is more R&B than rap. But, it’s the connection with his audience that sets him apart. He is not scared to talk about his feelings or emotions on tracks, and that’s why he is so popular with female music fans. 

Drake is from a different time and place than Hip-Hop artists of the 1990s, so we have to respect that. His music is more rounded. And he is similar to Kanye West in the way he has made his own niche in the music industry and is not limited to one style or genre.

Until next time, happy listening.

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About Corey Hoffman

Corey is a multi-instrumentalist who has played in numerous bands over the years, some good, some not so good. He has also written countless songs and recorded five albums in professional studios across America. Today he is a hobby musician but still loves the guitar after over 15 years of playing.

He considers his writing as a way to share what he has learned over the decades with younger generations ad always can't wait to get his hands on the latest gear.

He lives just outside New York with his wife Barbara and their two German Shepherds, Ziggy and Iggy.

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