26 Saddest Drake Songs of All Time, Ranked (2023)

If there’s one thing we can all agree on, it’s that Drake knows how to tug at our heartstrings. The “6 God” doesn’t shy away from baring his soul, and his vulnerability is a major reason why we love him.

Through his melodic, introspective tracks, Drake has a unique way of capturing life’s highs and lows, making us feel like he’s speaking directly to us.

So, grab a box of tissues and prepare for a heavy dose of Drake-induced feels – we’re about to embark on a heartfelt journey through the saddest Drake songs.

Related: Slow Drake Songs | Drake Love Songs

1. “Doing It Wrong” – Drake (2011)

🎵 Song Name: Doing It Wrong
🧑 Artist: Drake
💿 Album: Take Care (Deluxe)
📅 Release Date: 2011
🕒 Song Duration: 4 minutes 25 seconds

“Doing It Wrong” from Drake’s 2011 album Take Care (Deluxe) is a poignant reflection on a failing relationship and the struggle to let go. With its melancholic melody and impactful lyrics, it’s no wonder this song is considered one of Drake’s saddest.

The lyrics highlight the difficulty of acknowledging when things must change, with lines like “So cry if you need to, but I can’t stay to watch you.” Further, Drake delves into the concept of a disjointed generation that fears commitment in the line, “We live in a generation of not being in love and not being together.” 

“Doing It Wrong” resonates with listeners who’ve found themselves in similar situations, and remains a powerful anthem for emotional courage and authenticity.

2. “Redemption” – Drake (2016)

🎵 Song Name: Redemption
🧑 Artist: Drake
💿 Album: Views
📅 Release Date: 2016
🕒 Song Duration: 5 minutes 34 seconds

“Redemption” from Drake’s 2016 album Views is a heart-wrenching dive into the artist’s introspection on relationships and his struggles with commitment. Drake’s vulnerability shines through the lyrics, as he questions his decisions and past actions.

This song has resonated with listeners who can relate to its emotional intensity, making it one of Drake’s saddest songs. The elements of remorse, self-doubt, and yearning for redemption add profound depth to the track.

Moreover, Drake’s candidness in discussing his personal life has made a strong impact on his fans and listeners.

3. “Marvins Room” – Drake (2011)

🎵 Song Name: Marvins Room
🧑 Artist: Drake
💿 Album: Take Care (Deluxe)
📅 Release Date: 2011
🕒 Song Duration: 5 minutes 47 seconds

“Marvins Room” from Drake’s 2011 album Take Care (Deluxe) is undoubtedly one of his saddest songs. The track showcases the vulnerability of the rapper, delving deep into themes of loneliness, desperation, and unrequited love.

Through the somber lyrics, listeners feel the weight of Drake’s emotions as he drunkenly reaches out to an ex who is now with another man. The song’s impact on fans was significant and resonated with many who could relate to the heartbreak of losing someone they once loved.

Despite the sadness, “Marvins Room” still achieved great success, becoming iconic for not only its raw emotion but also the introspective storytelling that set Drake apart from his contemporaries.

4. “My Side” – Drake (2019)

🎵 Song Name: My Side
🧑 Artist: Drake
💿 Album: Care Package
📅 Release Date: 2019
🕒 Song Duration: 4 minutes 55 seconds

Drake’s “My Side” from his 2019 album Care Package is a poignant reflection on the difficulties of maintaining a long-distance relationship. The song’s melancholic tone emphasizes the singer’s emotions as he expresses his longing to connect more deeply with his partner.

Drake questions why their “relationship” must be built on such distance and why they can’t openly discuss their issues. Although “My Side” showcases the rapper’s vulnerabilites, it also adds another layer to the album’s narrative and leaves a lasting impact on listeners, making it one of Drake’s saddest and most relatable songs.

5. “I Get Lonely” – Drake (2019)

🎵 Song Name: I Get Lonely
🧑 Artist: Drake
💿 Album: Care Package
📅 Release Date: 2019
🕒 Song Duration: 4 minutes 14 seconds

“Care Package” certainly brought back sentimental moments for die-hard Drake fans. Nostalgic as it is, “I Get Lonely” stands out as one of the saddest songs on the album.

Featuring heart-rending lyrics that explore the feeling of loneliness even in fame, it’s a statement that resonates with many listeners. Drake’s emotional vulnerability is put on display as he sings, “Just like you, I get lonely.” His relatability and willingness to open up allows fans to feel a deeper emotional connection with the song.

“I Get Lonely” leaves an indelible mark in the world of sad Drake songs.

6. “From Time” Feat. Jhené Aiko (2013)

🎵 Song Name: From Time
🧑 Artist: Drake
🧑 Featured Artist(s): Jhené Aiko
💿 Album: Nothing Was The Same
📅 Release Date: 2013
🕒 Song Duration: 5 minutes 22 seconds

“From Time” by Drake featuring Jhené Aiko is a raw and introspective track from his 2013 album Nothing Was The Same. This melancholic tune dives into the complexities of relationships, self-love, and personal growth.

With lyrics like “I love me enough for the both of us”, the duo examines the push and pull of navigating love while dealing with personal insecurities. Fans widely consider it one of Drake’s saddest songs due to its vulnerability and relatable themes.

The impact on listeners is powerful, as many resonate with the song’s emotive exploration of love and life’s hardships.

7. “Teenage Fever” – Drake (2017)

🎵 Song Name: Teenage Fever
🧑 Artist: Drake
💿 Album: More Life
📅 Release Date: 2017
🕒 Song Duration: 3 minutes 40 seconds

In “Teenage Fever” from the 2017 album More Life, Drake channels his emotions of longing and regret through introspective lyrics. The song addresses a failed relationship and the difficulty of moving on.

Drake exposes his vulnerability, admitting that he both misses the past and fears the future, as captured in the line “This shit feels like teenage fever.” With the inclusion of Jennifer Lopez’s classic “If You Had My Love” chorus, it hints at the complexity of love, trust, and deception. “Teenage Fever” is considered one of Drake’s saddest songs due to its raw, emotional portrayal of heartache.

8. “Connect” – Drake (2013)

🎵 Song Name: Connect
🧑 Artist: Drake
💿 Album: Nothing Was The Same
📅 Release Date: 2013
🕒 Song Duration: 4 minutes 56 seconds

“Connect” by Drake from the 2013 album Nothing Was The Same is an introspective and somber track. At its core, “Connect” addresses failed communication and relationships, with lyrics like “How you talk all this shit and we still lack communication?” The song’s impact on listeners resonates due to its raw and honest emotions, making it one of the saddest Drake songs.

It showcases Drake’s vulnerability with lines such as “I’m just tryna connect with somethin’, babe” demonstrating a universal longing to connect despite life’s obstacles. Overall, the song speaks to the complex, often bittersweet nature of human relationships.

9. “Look What You’ve Done” – Drake (2011)

🎵 Song Name: Look What You’ve Done
🧑 Artist: Drake
💿 Album: Take Care (Deluxe)
📅 Release Date: 2011
🕒 Song Duration: 5 minutes 2 seconds

“Look What You’ve Done” is a heartfelt track from Drake’s 2011 album Take Care (Deluxe) that showcases the rapper’s vulnerability. The lyrics reveal Drake’s gratitude for the love and support he received from his family and friends during his early life struggles.

While it’s one of the saddest Drake songs, it highlights the impact loved ones have had on his life, as he reminisces about the past with lines like, “you knew that I was gon’ be somethin’.” The song’s strength lies in its emotional honesty and the message to appreciate the importance of relationships in shaping one’s life.

10. “Feel No Ways” – Drake (2016)

🎵 Song Name: Feel No Ways
🧑 Artist: Drake
💿 Album: Views
📅 Release Date: 2016
🕒 Song Duration: 4 minutes 1 seconds

“Feel No Ways” by Drake, from his 2016 album Views, is a melancholic track exploring the emotional turmoil of a failing relationship. The lyrics depict the struggle of letting go, with Drake questioning his partner’s loyalty and motives.

The sadness of the song resonates with listeners due to its raw and honest lyrics, highlighting how fame can complicate love. Its poignant lines like “I had to let go of us to show myself what I could do” suggest the necessity of self-discovery over maintaining a turbulent relationship.

11. “Fireworks” Feat. Alicia Keys (2010)

🎵 Song Name: Fireworks
🧑 Artist: Drake
🧑 Featured Artist(s): Alicia Keys
💿 Album: Thank Me Later
📅 Release Date: 2010
🕒 Song Duration: 5 minutes 13 seconds

“Fireworks” is a deeply introspective track off of Drake’s 2010 album Thank Me Later, featuring the soulful Alicia Keys. The song dives into the complexities of fame, personal relationships, and the longing for genuine love.

In the lyrics, Drake wonders about a life without money and its influence on his relationships, while Alicia Keys’ chorus emphasizes the continuous explosions of emotions and experiences in their lives. Despite the upbeat melody, “Fireworks” undoubtedly holds a melancholic undertone that resonates with listeners, making it one of Drake’s saddest songs as he explores the unpredictable and challenging nature of both fame and love.

12. “Trust Issues” – Drake (2019)

🎵 Song Name: Trust Issues
🧑 Artist: Drake
💿 Album: Care Package
📅 Release Date: 2019
🕒 Song Duration: 4 minutes 42 seconds

“Trust Issues” from Drake’s album Care Package encapsulates the vulnerability and emotional complexity that make it one of his saddest tracks. With an introspective narration of his struggles with trust and relationships, the lyrics reveal the darker side of fame.

Drake confesses that he chooses to drown his pain in alcohol and money, emphasizing his detachment from people. These raw emotions create a powerful impact on listeners, as we witness a star struggling to find genuine connections in the chaotic world around him.

“Trust Issues” remains an evocative example of Drake’s ability to candidly connect with his audience.

13. “Shot For Me” – Drake (2011)

🎵 Song Name: Shot For Me
🧑 Artist: Drake
💿 Album: Take Care (Deluxe)
📅 Release Date: 2011
🕒 Song Duration: 3 minutes 45 seconds

Diving into the depths of heartache, “Shot For Me” from Drake’s 2011 album Take Care (Deluxe) resonates with listeners as one of his saddest songs. Drake’s introspective lyrics reveal the challenges of a broken relationship, raw emotions, and clinging to the memories of the love once shared.

Taking a unique approach, Drake highlights both his own pain and the pain felt by his ex, showcasing true vulnerability. “Shot For Me” leaves a lasting impact on listeners.

Anyone who’s been through the tumultuous journey of love-gone-wrong can relate to the unwavering honesty and haunting melody of this unforgettable track.

14. “Jungle” – Drake (2015)

🎵 Song Name: Jungle
🧑 Artist: Drake
💿 Album: If You’re Reading This It’s Too Late
📅 Release Date: 2015
🕒 Song Duration: 5 minutes 20 seconds

“Jungle” is a soulful track from Drake’s 2015 album If You’re Reading This It’s Too Late, often regarded as one of his saddest songs. With its reflective lyrics and melancholic vibe, the song centers on the complexities of relationships.

Drake candidly explores vulnerability and seeks clarity in his connection with a significant other, ultimately questioning if they’re still good together. One of the reasons this song stands out is the raw emotion Drake conveys through his verses, as he admits to feeling lost and anxious about a relationship that seems to be slipping away. This resonates with listeners, allowing them to deeply connect with the song’s lyrics.

Additionally, Gabriel Garzón Montano’s emotive chorus adds to the track’s somber feel, further emphasizing the underlying sadness. Overall, “Jungle” showcases Drake’s ability to wear his heart on his sleeve, creating a powerful and poignant listening experience.

15. “Preach” Feat. PARTYNEXTDOOR (2015)

🎵 Song Name: Preach
🧑 Artist: Drake
🧑 Featured Artist(s): PARTYNEXTDOOR
💿 Album: If You’re Reading This It’s Too Late
📅 Release Date: 2015
🕒 Song Duration: 3 minutes 57 seconds

“Preach” by Drake, featuring PARTYNEXTDOOR, is a track from his 2015 album If You’re Reading This It’s Too Late. The song delves into themes of hedonistic pursuits and relationship complications, with Drake reflecting on how fame has impacted his ability to maintain meaningful connections.

The introspective lyrics take the listener on a journey through Drake’s experiences in Miami and the consequences of the fast-paced, chaotic lifestyle. Despite its somber undertones, “Preach” remains one of Drake’s saddest tracks with its haunting melody and relatable examination of love, fame, and self-reflection.

16. “The Real Her” Feat. Lil Wayne, André 3000 (2011)

🎵 Song Name: The Real Her
🧑 Artist: Drake
🧑 Featured Artist(s): Lil Wayne, André 3000
💿 Album: Take Care (Deluxe)
📅 Release Date: 2011
🕒 Song Duration: 5 minutes 21 seconds

“The Real Her” from Drake’s album Take Care (Deluxe) is a melancholic song that delves into the complexities of romantic relationships. Featuring Lil Wayne and André 3000, the lyrics discuss the familiar feeling of meeting someone new but feeling like you already know the real them.

The song’s impact on listeners stems from its raw emotions, making it one of the saddest Drake songs. “The Real Her” emphasizes the idea of finding someone with desirable qualities, but not quite fulfilling the emotional connection you’re seeking, as Drake sings, “You got that shit that somebody would look for, but won’t find“.

17. “Wednesday Night Interlude” Feat. PARTYNEXTDOOR (2015)

🎵 Song Name: Wednesday Night Interlude
🧑 Artist: Drake
🧑 Featured Artist(s): PARTYNEXTDOOR
💿 Album: If You’re Reading This It’s Too Late
📅 Release Date: 2015
🕒 Song Duration: 3 minutes 32 seconds

When diving into the melancholic world of “Wednesday Night Interlude” by Drake (Featuring: PARTYNEXTDOOR) from the 2015 album If You’re Reading This It’s Too Late, one discovers a raw exploration of loneliness and longing. It’s often considered one of Drake’s saddest songs, resonating with listeners who’ve experienced similar feelings.

PARTYNEXTDOOR delivers vulnerable lyrics, expressing the pain of wanting someone while feeling lonely on a mundane Wednesday night. The song’s impactful background of dreamy production by Ekali and PARTYNEXTDOOR amplifies these emotions, leaving fans with a masterpiece that lingers long after the final notes fade.

18. “Summers Over Interlude” Feat. Majid Jordan (2016)

🎵 Song Name: Summers Over Interlude
🧑 Artist: Drake
🧑 Featured Artist(s): Majid Jordan
💿 Album: Views
📅 Release Date: 2016
🕒 Song Duration: 1 minutes 46 seconds

“Summers Over Interlude” by Drake, featuring Majid Jordan, appears on his 2016 album, Views. This melancholic track reflects on the end of summer and the accompanying end of a relationship.

With lyrics like, “Days in the sun and nights in the rain / Summer is over, simple and plain,” it evokes the bittersweet feeling of change. The repetition of “I don’t feel the same” signifies the difficulty in moving on.

Known as one of Drake’s saddest songs, “Summers Over Interlude” resonates with listeners who have experienced heartbreak and the inevitable passage of time.

19. “Finesse” – Drake (2018)

🎵 Song Name: Finesse
🧑 Artist: Drake
💿 Album: Scorpion
📅 Release Date: 2018
🕒 Song Duration: 3 minutes 2 seconds

“Finesse” from Drake’s 2018 album Scorpion is truly one of his saddest songs, showcasing a vulnerable side of the artist. The lyrics delve into emotional turmoil as he grapples with conflicting desires and feelings.

Lines like “I want my baby to have your eyes” and “emotions running high” reveal an inner struggle. The repeated phrase “It takes some finesse” might suggest the difficulty in navigating complex relationships.

Listeners can relate to the melancholic honesty, making this song an impactful piece in the album. With its introspective nature, “Finesse” holds a special place in Drake’s discography.

20. “Pound Cake / Paris Morton Music 2” Feat. JAY-Z (2013)

🎵 Song Name: Pound Cake / Paris Morton Music 2
🧑 Artist: Drake
🧑 Featured Artist(s): JAY-Z
💿 Album: Nothing Was The Same
📅 Release Date: 2013
🕒 Song Duration: 7 minutes 13 seconds

The intriguing track “Pound Cake / Paris Morton Music 2” by Drake, featuring JAY-Z, comes from the album Nothing Was The Same released in 2013. A notable aspect of the song is its introspective nature, which delves deep into the world of fame and success.

The lyrics reveal Drake’s thoughts on his career and how the industry has perceived him. The poignant track also touches on themes of loyalty and personal growth.

Many fans consider this song one of the saddest in Drake’s repertoire, as it provides a glimpse into the darker aspects and mental battles of the rap mogul’s life.

21. “Do Not Disturb” – Drake (2017)

🎵 Song Name: Do Not Disturb
🧑 Artist: Drake
💿 Album: More Life
📅 Release Date: 2017
🕒 Song Duration: 4 minutes 44 seconds

In 2017, Drake gifted fans with “Do Not Disturb“, a melodic and introspective track off his More Life album, and easily one of the saddest Drake songs. The song showcases vulnerability as he opens up about dealing with fame and expectations.

With lyrics like “Wakin’ up to public statements about my private life“, Drake allows listeners to feel the weight of his celebrity status. This emotional honesty, combined with a catchy beat, had a significant impact on the fans, showing that even superstars like Drake grapple with self-doubt, creating an even stronger connection with his audience.

22. “Too Much” Feat. Sampha (2013)

🎵 Song Name: Too Much
🧑 Artist: Drake
🧑 Featured Artist(s): Sampha
💿 Album: Nothing Was The Same
📅 Release Date: 2013
🕒 Song Duration: 4 minutes 22 seconds

“Too Much” from Drake’s 2013 album Nothing Was The Same features the soulful vocals of Sampha, amplifying the song’s emotional depth. This track is considered one of Drake’s saddest songs, as it delves into his personal struggles with success, family, and self-doubt.

The heartfelt lyrics touch on Drake’s desire to escape negative thoughts as well as issues within his family. The chorus, sung by Sampha, illustrates the concept of overthinking and the need to slow down in our fast-paced lives.

With its raw honesty and introspection, “Too Much” has left a strong impact on listeners since its release.

23. “You & The 6” – Drake (2015)

🎵 Song Name: You & The 6
🧑 Artist: Drake
💿 Album: If You’re Reading This It’s Too Late
📅 Release Date: 2015
🕒 Song Duration: 4 minutes 25 seconds

“You & The 6” from Drake’s 2015 album If You’re Reading This It’s Too Late is indeed one of his saddest songs. It showcases an intimate, heartfelt conversation between Drake and his mother.

With its deep and honest lyrics, listeners can relate to the emotional dilemmas of balancing career, family, and personal life. Drake acknowledges his vulnerability amidst his success and constantly addresses his connection with his family, especially his mother’s unconditional support. He highlights their influence on his upbringing when he raps, “You and the six raised me right, that shit saved my life.” This song resonates with audiences by capturing the raw emotions and struggles one may face while achieving success.

“You & The 6” ultimately serves as a touching ode to Drake’s mother and a reflection of the deep bond they share.

24. “Club Paradise” – Drake (2019)

🎵 Song Name: Club Paradise
🧑 Artist: Drake
💿 Album: Care Package
📅 Release Date: 2019
🕒 Song Duration: 4 minutes 44 seconds

“Club Paradise” from Drake’s album Care Package is a heartfelt confessional track reflecting on the perils of fame, lost love, and the pressures of success. Often ranked among the saddest Drake songs, listeners are immediately drawn into the introspective narrative.

The lyrics depict Drake’s struggle to reconcile his public persona with personal relationships that have suffered due to his rise to stardom. Club Paradise invites the audience into Drake’s vulnerable state, revealing the heartache beneath the glitz.

The song serves as a reminder that even in the throes of fame, one shouldn’t forget their roots.

25. “Successful” Feat. Trey Songz, Lil Wayne (2009)

🎵 Song Name: Successful
🧑 Artist: Drake
🧑 Featured Artist(s): Trey Songz, Lil Wayne
💿 Album: So Far Gone
📅 Release Date: 2009
🕒 Song Duration: 6 minutes 15 seconds

In 2009, Drake released “Successful” from the album So Far Gone, featuring Trey Songz and Lil Wayne. The song delves into the artists’ desire for success, which they believe encompasses money, cars, clothes, and women.

With its raw and emotional lyrics, “Successful” stands as one of Drake’s saddest songs, highlighting the loneliness and emptiness often experienced at the top. Despite the seemingly materialistic focus, the song speaks to the universal struggle of chasing success, leaving a deep impact on listeners.

Drake’s powerful storytelling and emotive delivery make “Successful” a memorable, introspective hit from his early career.

26. “The Resistance” – Drake (2010)

🎵 Song Name: The Resistance
🧑 Artist: Drake
💿 Album: Thank Me Later
📅 Release Date: 2010
🕒 Song Duration: 3 minutes 45 seconds

“The Resistance” from Drake’s 2010 album Thank Me Later delves into the struggles of newfound fame and staying true to one’s roots. With lyrics lamenting lost connections and the pressure of never changing, it’s one of Drake’s saddest tracks.

Notable lines such as “What am I afraid of? This is supposed to be what dreams are made of,” convey feelings of surrealism tied to success. Drake explores personal vulnerability in lyrics about his family, questioning if he’s traded his free time for the limelight, and seeking closure.

Ultimately, “The Resistance” beautifully captures the introspective turmoil of an artist rising to fame.