With Valentine’s Day around the corner, I decided to make an unusual list: not of all-time great love songs, but all-time great anxious love songs. Anxious love songs typically involve conflict—around unrequited passion, cheating, or loss—where the singer often feels something unresolved. Most of my favorite anxious love songs are exceptionally well-known—classic, even—so this list shifted to some of the more unusual, less canonized recordings that deserve greater recognition on lists of love songs.
The artists are all well known, but I maintain that the songs deserve bigger audiences—or, in some cases, they have big audiences, but aren’t considered classics when they should be. This list features songs representing R&B, country, pop, jazz, blues, rock, hip hop, and folk, sometimes with a mix of multiple styles.
10. Mariah Carey – “The Roof (Back in Time)”
In recent years, Mariah Carey has been receiving long-overdue recognition for her contributions to the music industry, including being the MusiCares 2026 Person of the Year. However, in the 1990s, beyond the control of her label boss and one-time husband, Tommy Mottola, many underestimated her talents as a singer–and especially as a songwriter. “The Roof (Back in Time)”, originally featured on her 1997 album Butterfly, is a standout underappreciated 1990s single.
Carey’s acumen with moody intimacy is on full display here, and it makes her versatility more apparent when contrasted with upbeat hits like “Emotions” and “Fantasy”. According to her 2020 memoir, she wrote the lyrics to this song about her relationship with baseball player Derek Jeter. The anxious love comes from the passion of the secret affair and her memories of feeling safe and secure. The extended version featuring rappers Mobb Deep enhances the gritty feel of the song and video, and it deserves much wider hearing.
9. Tracy Lawrence – “Paint Me a Birmingham”
In the mid-2000s, all-time great country story songs like Brad Paisley and Alison Krauss’ “Whiskey Lullaby”, Kenny Chesney’s “There Goes My Life”, and Tim McGraw’s “Live Like You Were Dying” were everywhere. Although Tracy Lawrence’s 2004 hit “Paint Me a Birmingham” is less remembered, it absolutely deserves mention in that company. Lawrence emerged in the 1990s with hits like “Alibis” and “Time Marches On”, but he’s less beloved than contemporaries like McGraw. This song, though, deserves a place in the country pantheon.
One of my all-time favorite songs about grief, “Paint Me a Birmingham” is ambiguous: is the singer grieving a breakup with or the death of a loved one? Either way, the song deeply resonates for anyone who’s experienced deep loss. When Lawrence sings, “I said, ‘If there’s any way you can, could you paint me back into her arms again?’” it hits hard. I don’t care who you are or what kind of music you listen to, this is a great song–a great country song, yes, but one deserving of a far bigger audience.
8. Bobby “Blue” Bland – “Stormy Monday Blues”
Smooth, nuanced, and impassioned, all in one song: Bobby “Blue” Bland’s emotional range made recordings like this special. Released in 1962, Bland’s version of T-Bone Walker’s blues standard rearranges the song into what sounds like an intimate late-night jam session. Despite being less remembered than Bland classics like “Ain’t No Love in the Heart of the City”, Bland’s shading of the lyrics’ meaning with different tones and timbres makes this an exemplary R&B recording for its era and beyond.
The anxiety in the lyrics stems from longing for a lover and from praying for her to come home. The intensity and complexity of Bland’s performance make it sound like he’s carrying a different kind of blues feeling than Walker in the original. “Stormy Monday Blues” makes a solid case for Bland as an all-time great R&B and blues singer, but more quietly than many of his better-known recordings do.
7. Tracy Chapman – “For My Lover”
There are no bad songs on singer-songwriter Tracy Chapman’s 1988 self-titled debut, and “For My Lover” is one of the album’s most chilling tracks. Chapman’s story of queer love, incarceration, and ensuing questions holds up as one of the best rock or folk recordings of its time. In fact, the song is so strong that the reverb-heavy drums don’t distract as much as they do on many recordings of the 1980s.
As I noted in an article for PopMatters, scholar Heather E. Harris calls twisted love one of the album’s key lyrical themes, and the anxiety around the relationship (“Is this love worth the sacrifices I make?”) adds urgency to a recording filled with tension and resignation. The earliest recording of the song appeared in 1986 as a solo track, but the 1988 album track reached millions of listeners and helped establish Tracy Chapman as one of the decade’s greatest albums. Chapman has written many socially conscious songs, but this is one of the best.
6. Sarah Vaughan – “Darn That Dream”
Jazz legend Sarah Vaughan’s voice was beyond extraordinary–it’s one of the most tonally unusual and capacious instruments I’ve ever heard, even beyond its superhuman range. Her inflections, enormous breath control, and insinuating vibrato could caress as well as mock words, and whether her 1958 recording of “Darn That Dream” for the album No Count Sarah sounds sincere depends on whoever hears it.
What is clear, however, is the haunting quality of the recording, with Vaughan employing a greater variety of tonal colors than any singer I’ve heard sing this song, including Billie Holiday and Dinah Washington. Holiday was better known for personalized interpretations of lyrics, and Ella Fitzgerald for melody and rhythm, but Vaughan might be the greatest singer in jazz specifically, for a combination of both. Her version of “Darn That Dream” exemplifies that tendency, conveying the unease and anxiety of an unrequited romance.
5. Michael Jackson – “Give in to Me”
This might sound like sacrilege, but the best rock track Michael Jackson ever made is not “Beat It”. It also isn’t “Dirty Diana”. It’s “Give in to Me”, a forgotten single from his most mature artistic statement, Dangerous, and a rare (relative) flop from his hitmaking heyday. Of his rock tracks, Jackson sounds most in his element here, the singer desperately grasping at whatever power he can have over a woman.
His conviction–the anxiety and stress manifesting in his vocals–is well matched by a guest guitarist from Guns N’ Roses. Slash, even more than Eddie Van Halen on “Beat It”, enhances this record. Both Jackson’s vocals and the guitar pyrotechnics fit this record like one of Jackson’s famed white sequin gloves. Dangerous had some of the funkiest dance tracks, best singing, and best songwriting that Jackson ever did, but “Give in to Me” stands out even on such an extraordinary–and often underrated–album.
4. Sam Cooke – “(Somebody) Ease My Troublin’ Mind”
Jerry Wexler, the Atlantic Records producer behind classic work from Aretha Franklin and Ray Charles, once called Sam Cooke “the best singer who ever lived, no contest” (quoted in Peter Guralnick, Sweet Soul Music: Rhythm and Blues and the Southern Dreams of Freedom, Harper & Row, 1986). Cooke’s singing was at its most impassioned, however, on his gospel records with the Soul Stirrers before he became an iconic pop star.
Towards the end of his jam-packed but too brief career and life, his secular recordings began showing more audible gospel influences, including on “A Change Is Gonna Come” and “(Somebody) Ease My Troublin’ Mind”. The latter is a startling performance of confessing the blues, with Cooke’s smooth pop sensibility combined with his raw rasp and trademark melisma, resulting in a chilling recording of Cooke at his best. He presents the lyric with a different kind of desperation than that on other recordings on this list, sounding both understated and soaring, and the recording deserves much greater listenership.
3. Sugarland – “Stay”
I am not claiming that country group Sugarland is greater than Sam Cooke or Sarah Vaughan, but their 2007 single, “Stay”, is easily one of the best smash hits of the twenty-first century in country music–or any genre. Jennifer Nettles’ devastating vocal, with overwhelming determination and pathos, knocks me out every time I hear this song, and the minimal arrangement and production put that vocal front and center.
The singer’s anxiety and internal struggle about being a “side chick” to a man in a committed relationship are relatable to many. By the end, however, her departure is empowering. When Nettles sings, “I’m so tired of being lonely / You can’t give me what I need,” the conviction in her voice sounds palpable, raw, candid, and astonishing. In a genre known for storytelling, “Stay” is a standout all these years later. No wonder the longest-running country music blog, Country Universe, called it one of the 20 greatest singles of its first 20 years.
2. Willie Nelson – “Can I Sleep in Your Arms”
The year 1975 marked the emergence of Willie Nelson as a powerhouse artist–not just songwriter–in country music with the unlikely blockbuster album, Red Headed Stranger. A few of its tracks are all-time great performances, including “Blue Eyes Crying in the Rain.” Like that classic, “Can I Sleep in Your Arms” was not written by Nelson, but its stark, bare bones production stood out from what some labeled as gaudy and excessive tendencies in mainstream country.
This song was not a hit, but it deserves mention on this list for its understated depiction of the singer’s angst and desperation–not merely longing–for sex and companionship. Nelson’s often-acknowledged idiosyncratic phrasing is a big reason this record, written by legendary country songwriter Hank Cochran and first made famous by Jeannie Seely, deserves iconic status. In the context of its album and beyond, “Can I Sleep in Your Arms” is a stunner.
1. Janet Jackson – “Miss You Much”
Hear me out: this song may be a classic to Janet Jackson fans, but since Justin Timberlake ripped off part of Jackson’s bra at the Super Bowl halftime show in 2004, songs like “Miss You Much” have not received nearly the amount of love that they deserve. I would argue that more than any other Janet Jackson hit of its time, this song makes the case for Jackson as the Queen of Pop ahead of her contemporaries, including Madonna and Whitney Houston.
The follow-up to Jackson’s 1986 breakthrough album, Control, 1989’s Rhythm Nation 1814, contains several huge hits, including “Rhythm Nation” and “Love Will Never Do (Without You)”. However, the especially ebullient and forceful “Miss You Much” is one of the greatest pop records of any era. The lyrics, the vocals, and the beat positively itch with aggressive longing. More than any other song on this list, “Miss You Much” epitomizes the anxious love song. As Jackson says, “That’s the end??”