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10 Best Tom Waits Love Songs, Ranked (2023)

Welcome fellow music connoisseurs and love song enthusiasts. Get ready to embark on a captivating journey as we dive into the songs that truly capture the essence of one of the most enigmatic and talented singer-songwriters of our time, Tom Waits.

Through his gravelly voice and imaginative narrative, these 10 heart-melting tunes will surely tug at the chords of your heart all while leaving you longing for even more.

So curl up with that special someone or grab a glass of nostalgia as we explore the undeniable beauty that lies within Tom Waits’ best love songs!

1. “Martha” (1973)

Album art
🎵 Song Name: Martha
🧑 Artist: Tom Waits
💿 Album: Closing Time (Remastered)
📅 Release Date: 1973
🕒 Song Duration: 4 minutes 29 seconds

In “Martha,” from Tom Waits’ 1973 album “Closing Time (Remastered),” we embark on an emotional journey through the depths of love and regret. The lyrics tell a heart-wrenching story of a man longing to rekindle the flame with his former lover, Martha.

Waits’ raspy yet soothing voice perfectly captures the raw emotion behind the plea, with lines like “Those were days of roses, poetry, and prose.” At number 1 on our list, “Martha” showcases Waits’ incredible ability to tap into the very core of human love and nostalgia through his music.

2. “Hold On” (1999)

Album art
🎵 Song Name: Hold On
🧑 Artist: Tom Waits
💿 Album: Mule Variations (Remastered)
📅 Release Date: 1999
🕒 Song Duration: 5 minutes 34 seconds

Hold on tight, fellow music-lovers, because No. 2 on our list of the best Tom Waits Love Songs is “Hold On” from his 1999 album Mule Variations (Remastered).

A fan-favorite, this track is a soaring testament to the resilience of love in even the toughest of times. Waits weaves an emotional tale of finding and clinging onto the hope and love amidst hardships, urging his listeners to “Hold On”.

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As the song unfolds with raw storytelling and Tom’s signature raspy voice, we’re reminded that no matter the obstacles life and love may throw our way, there’s always a reason to hold on.

3. “(Looking For) The Heart Of Saturday Night” (1974)

https://www.youtube.com/watch?v=f7UHd7NVegE
Album art
🎵 Song Name: (Looking For) The Heart Of Saturday Night
🧑 Artist: Tom Waits
💿 Album: The Heart Of Saturday Night (Remastered)
📅 Release Date: 1974
🕒 Song Duration: 3 minutes 53 seconds

“Looking For (The Heart Of Saturday Night)” by Tom Waits delivers a captivating tale of a romantic quest in search of the essence of a perfect Saturday night. Waits places us alongside a character that traverses the night with excitement and anticipation, singing “Will this be the one that you’re giving your heart to?”.

The album’s title track showcases Waits’ unmistakable storytelling ability and raspy voice, which together spin an atmosphere of hope, longing, and nighttime adventures. As number 3 on our Top 10 Tom Waits Love Songs, this tune beautifully encapsulates the feeling of seeking true love and endless possibilities on a Saturday night.

4. “Jersey Girl” (1980)

Album art
🎵 Song Name: Jersey Girl
🧑 Artist: Tom Waits
💿 Album: Heartattack And Vine (Remastered)
📅 Release Date: 1980
🕒 Song Duration: 5 minutes 12 seconds

Coming in at number 4 on our list of the best Tom Waits Love Songs is “Jersey Girl.” This 1980 classic highlights Waits’ raw and tender side, with lyrics that paint a vivid picture of his love for a woman from New Jersey. In a departure from his typically gritty storytelling, “Jersey Girl” showcases a backdrop of romance and intimacy with lines like “Don’t the sun look angry through the trees?” and “Sha la la, la la la la.” With its captivating tales of late-night drives and emotional vulnerability, “Jersey Girl” is a heartwarming ode to simple, unconditional love.

5. “Long Way Home” (2006)

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🎵 Song Name: Long Way Home
🧑 Artist: Tom Waits
💿 Album: Orphans: Brawlers, Bawlers & Bastards (Remastered)
📅 Release Date: 2006
🕒 Song Duration: 3 minutes 10 seconds

“Long Way Home” from Tom Waits’ 2006 album “Orphans: Brawlers, Bawlers & Bastards (Remastered)” captures the raw emotion and vulnerability of love, earning its spot at number 5 on our list of the best Tom Waits Love Songs. Waits croons his way through the track, painting a picture of a romantic journey where the arduous path of love only adds to its beauty.

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The striking imagery and heartfelt lyrics convey the willingness of the protagonist to go any distance for the one who holds his heart. A true masterpiece that showcases Waits’ unique storytelling prowess.

6. “Closing Time” (1973)

Album art
🎵 Song Name: Closing Time
🧑 Artist: Tom Waits
💿 Album: Closing Time (Remastered)
📅 Release Date: 1973
🕒 Song Duration: 4 minutes 20 seconds

In “Closing Time“, our number 6 pick of Tom Waits Love Songs, Waits melodiously paints a picture of a dimly lit bar after last call, where patrons are wistful and weary. Amidst the melancholic atmosphere, the song beautifully conveys a lover’s yearning to hold on just a moment longer, as the world fades around them.

This track’s signature romantic, late-night vibes encapsulate a tender, vulnerable intimacy only found in those fleeting moments, cementing “Closing Time“as a must-have on any Waits-powered playlist.

7. “San Diego Serenade” (1974)

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🎵 Song Name: San Diego Serenade
🧑 Artist: Tom Waits
💿 Album: The Heart Of Saturday Night (Remastered)
📅 Release Date: 1974
🕒 Song Duration: 3 minutes 30 seconds

In “San Diego Serenade“, Tom Waits beautifully captures the feeling of appreciating love through the lens of absence or loss. This 1974 song from “The Heart of Saturday Night (Remastered)” offers a heartfelt confession of realizing the importance of someone, only after they’re gone.

Waits compares these realizations through striking imagery—such as not knowing true love until it’s too late. This heart-wrenchingly relatable track earns its place as number 7 out of 10 on our list of the best Tom Waits Love Songs.

8. “Grapefruit Moon” (1973)

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🎵 Song Name: Grapefruit Moon
🧑 Artist: Tom Waits
💿 Album: Closing Time (Remastered)
📅 Release Date: 1973
🕒 Song Duration: 4 minutes 45 seconds

In the mesmerizing ode “Grapefruit Moon“, Tom Waits weaves a tale of a love that is as beautiful and tantalizing as a “grapefruit moon“. His unique voice captures the essence of a bittersweet love story that endures against all odds.

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Enveloped by a late-night barroom ambience, it depicts a longing that’s enhanced by the mysterious and seductive lunar presence. Haunting piano melodies accompany the tender lyrics, echoing the dreamy and melancholic emotions that linger within.

It’s a dazzling portrayal of the raw, captivating power of love, earning its spot at number 8 in my list of Tom Waits’ best love songs.

9. “Green Grass” (2004)

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🎵 Song Name: Green Grass
🧑 Artist: Tom Waits
💿 Album: Real Gone (Remastered)
📅 Release Date: 2004
🕒 Song Duration: 3 minutes 12 seconds

Coming in at number 9 on our list of the best Tom Waits Love Songs is “Green Grass” from the album “Real Gone (Remastered)” released in 2004. This haunting melody paints a picture of a nostalgic, bittersweet love.

Waits’ gravelly voice and poetic lyrics take listeners on a stroll through a world of faded memories, implying both the enduring and the transient nature of love. The line “Don’t say good-bye to me, describe the sky to me” is a poignant reminder of how lovers would do anything to hold on to what once was.

10. “Picture In A Frame” (1999)

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🎵 Song Name: Picture In A Frame
🧑 Artist: Tom Waits
💿 Album: Mule Variations (Remastered)
📅 Release Date: 1999
🕒 Song Duration: 3 minutes 40 seconds

Sitting at number 10 on our list of the best Tom Waits Love Songs is the tender and soulful “Picture In A Frame.” This romantic ballad from Tom Waits’ 1999 album, “Mule Variations (Remastered),” tells the story of two lovers bonded so deeply that their love is elegantly immortalized in a photo frame. Waits sings about waiting, longing, and finally being able to share his life with the one he loves.

With a delightful blend of raw emotion and poetic simplicity, “Picture In A Frame” serves as a heartfelt tribute to love that can stand the test of time.