Beyond the Hits: 10 Madonna Songs Worth Digging Up
From B-sides to hidden album tracks, these deep cuts still shine.
Sure, we all know “Like a Virgin,” “Into the Groove,” and “Material Girl” — but Madonna’s ’80s catalog is way deeper than just the hits. Tucked away on albums, B-sides, soundtracks, and even a few unreleased gems, there’s a whole other side to early Madonna that hardcore fans swear by. These tracks may not have topped the charts, but they show off her range — from raw dance-floor energy to heartfelt ballads and everything in between.
So if you think you’ve heard all the essential Madge from the ‘80s… think again. Here are 10 underrated tracks that totally deserve a spot on your next playlist.
1. I Know It (1983)
From Madonna’s debut album, Madonna, “I Know It” is one of those early tracks that perfectly captures her rising-star energy. It’s not as famous as “Holiday” or “Borderline,” but it definitely holds its own with its punchy synths and that catchy, danceable beat.
Lyrically, it’s all about heartbreak with a side of pride. She knows her lover’s done with her, and yeah, she’s hurting — but she’s not about to fall apart over it. There’s a quiet confidence to it, and that theme of self-preservation shows up a lot in her early music. Totally underrated and pure early ‘80s pop.
2. Shoo-Bee-Doo (1984)
This one’s from Like a Virgin and is probably the most stylistically different song on the album. It’s got a soft, jazzy, doo-wop vibe — think ’50s prom slow-dance but with an ’80s twist. The chorus is super cute with Madonna cooing “Shoo-bee-doo-bee-doo, ooh la la,” and there’s even a killer sax solo by Lenny Pickett (fun fact: he’s the longtime sax guy from SNL).
The lyrics are simple — just Madonna telling someone to take a chance on her love — but it’s sweet and heartfelt. It never got single treatment in the U.S., but it was used as a B-side in Europe. Definitely one of those early hidden gems that shows her softer side.
3. Sidewalk Talk (1984)
Even though this track was released under the name Jellybean Benitez (Madonna’s producer and boyfriend at the time), it’s basically a Madonna song in disguise. She wrote it, and her vocals are all over it — especially in the chorus and background. The lead vocals were officially done by Catherine Buchanan, but a lot of fans think Madonna sings way more than she’s credited for.
Musically, it’s a funky little synth-pop banger — bright, bouncy, and super danceable. It sounds exactly like what you’d expect from the Madonna/Like a Virgin era. It hit No. 1 on the dance charts and remains a fan favorite, even if it’s a bit of a hidden track in her catalog.
4. Gambler (1985)
This one’s a deep cut from the Vision Quest soundtrack — same movie as “Crazy for You” — and it’s got serious energy. Madonna wrote it herself, and it’s full of fast-paced synths, drum machines, and this fiery, punky vibe. It’s basically her shouting “I do what I want!” in song form.
The lyrics are all about being independent and not letting anyone else control your path — classic Madonna attitude. Even though it wasn’t released as a single in the U.S. (reportedly due to label politics), it did really well internationally, especially in the UK. She only performed it once live, on the Virgin Tour, and fans still talk about it.
5. Each Time You Break My Heart (Demo) (1986)
Here’s a cool behind-the-scenes moment: Madonna co-wrote and produced this song during the True Blue sessions but ended up giving it to Nick Kamen, a model-turned-singer she helped launch. She even sang backing vocals on his version.
Her demo leaked later and fans instantly loved it — it sounds like vintage True Blue with glossy production and heartbreak lyrics. The song’s about someone who’s hurt her over and over, but she keeps coming back. You know, classic pop heartbreak. Even though her version never got an official release, it’s one of her most beloved unreleased tracks.
6. Where’s the Party (1986)
Off True Blue, this song is all about forgetting your problems and heading straight to the dance floor. It’s pure joy — with synths, a killer beat, and Madonna just wanting to let loose. It’s got a carefree, rebellious tone that fans loved, even though it was never released as a single.
She said it reflected how she felt about fame at the time — everyone expected so much from her, but she just wanted to have fun. It was performed on a few tours and even remixed for a promo release. A feel-good, underrated bop.
7. Can’t Stop (1987)
Buried on the Who’s That Girl soundtrack, “Can’t Stop” is a total dancefloor jam. It’s got a Motown feel blended with Madonna’s upbeat 80s pop style. It’s fast-paced, super catchy, and the hook (“Can’t stop thinkin’ about you, babe”) is impossible to get out of your head.
She co-wrote it with Stephen Bray, and he later said he thought this one should’ve been a single. It’s got that “early Madonna falling head-over-heels” vibe, with some real emotional urgency under the pop sheen. Definitely deserves more love.
8. Promise to Try (1989)
Now we shift into something way more emotional. “Promise to Try” is one of the most personal songs Madonna’s ever recorded — a quiet, piano-driven ballad about her mom, who died when Madonna was a little girl.
It’s raw and stripped down — just her and a piano, really — and she sings with such tenderness and pain. The lyrics are like a letter to her younger self, trying to stay strong but still grappling with loss. It’s not a radio hit or a club track, but it’s beautiful and shows a whole different side of her artistry.
9. Spanish Eyes (1989)
Also from Like a Prayer, “Spanish Eyes” (or “Pray for Spanish Eyes” depending on the edition) is haunting and heavy. It touches on death, violence, and faith — topics Madonna wasn’t afraid to tackle at this point. Some fans think it’s about gang violence or possibly the AIDS crisis, though Madonna never gave a definitive answer.
Musically, it’s dramatic and emotional, with strings, horns, and a slowly building intensity. Her vocals are powerful here — not polished, but felt. It’s one of her most underrated serious songs and really rounds out the emotional depth of the album.
10. Supernatural (1989)
Here’s one of Madonna’s weirdest and most fun deep cuts. “Supernatural” was originally a B-side to “Cherish” and later appeared on a Japanese edition of Like a Prayer. It’s a funky, playful track — and yes, it’s literally about hooking up with a ghost.
The production is super late-80s with layered synths and echoey vocals that give it a kind of spooky/sexy vibe. It’s not serious, but that’s the point — it’s Madonna being cheeky and experimental. A total fan-favorite oddball track.
Whether it’s a lost demo, a soundtrack one-off, or an overlooked album track, these songs prove that Madonna’s deep cuts are just as iconic (and sometimes even more interesting) than her biggest hits. They capture her boldness, vulnerability, and creative spark in ways casual listeners might have missed.
So go ahead — dig a little deeper into her discography. You’ll probably find a new favorite or two.