Don McLean Best Songs: TOP 10 Hits
If you want the ultimate time machine to take you 50–60 years into the past, to a time when things felt simpler, there was less stress, the air was cleaner, and the world just seemed like a happier place — Don McLean’s music is exactly what you need in your life.
Mostly known for his popular hits “American Pie” and “Vincent,” he’s far from a one-hit wonder. If you’re not yet familiar with his other amazing songs, this collection is the perfect place to start.
Enjoy Don McLean Best Songs chart – his TOP 10 hits. Discover incredible music that’s both timeless and so beautifully nostalgic, you’ll want to play it over and over again.
Don McLean Best Songs
These are carefully handpicked songs from Don McLean. In my book, these are his greatest hits. I’ve ranked them from ten to one — but don’t let that make you like some of them less than others. Every single track here is special.
10. Don McLean – Castles in the Air
“Castles in the Air” is a Don McLean classic, and it has a bit of an interesting history. It first appeared on his debut album Tapestry in 1970, but it’s the re-recorded version from 1981’s Believers that really took off. If you go now to Spotify and check the plays counter, it’s the newer version that has millions of plays. I love both recordings equally, and it’s obvious that this song is definitely one of his best.
9. Don McLean – Empty Chairs
If you’ve ever had your heart broken, you’ll get what “Empty Chairs” is about. In his signature fashion – through deep, honest lyrics and beautiful melody, Don McLean tells a story of a relationship that wasn’t meant to be. This intimate ballad from the American Pie album feels very personal and truly moving. Despite bringing in the genuine feeling of sadness it sounds incredibly poetic. It’s one of the most emotionally resonant songs in his entire catalog.
8. Don McLean – Sea Man
“Sea Man” is one of the most underrated gems Don McLean repertoire. It’s not his usual track, it doesn’t follow the melodic pattern he is know for. There’s literally no instruments in the first half of the song, other than the man’s voice. This catches listeners by surprise right away, as they focus on the lyrics. If you want to truly discover McLean’s artistry, his powerful storytelling side – this is a must-listen track.
7. Don McLean – Crying
Originally written by Roy Orbison, “Crying” was brought back to the spotlight by Don McLean in the late ’70s. This version became very popular and even reached No. 1 in the UK. Don didn’t just cover this song he made it his own. This just shows that McLean wasn’t just a great songwriter but also an incredible interpreter of other people’s work. This song absolutely earns its place in the Top 10 because it’s one of those rare covers that feels just as special as the original.
6. Don McLean– Winter Has Me In Its Grip
This song might not get as much play-time as “American Pie” or “Vincent,” but “Winter Has Me In Its Grip” is a hidden beauty from the same 1971 album. It’s a tender, introspective, and poetic composition that creates a vivid picture in you head. The metaphor of a cold winter is such a great lyrical find. The way how effortlessly this song captures a mood many people know and relate to, easily makes it worthy being in the TOP 10 chart.
5. Don McLean – Chain Lightning
Released later in McLean’s career, “Chain Lightning” shows that genuine artistry knows no age. It was recorded in Nashville with a more polished, country-influenced sound. Musically and lyrically, it strikes just as hard as his other popular songs. Give it a few listens – and it will grow on you even more, I promise. No wonder it became a fan favorite. Another track that proves McLean was never a one-hit wonder, and fully deserves its spot in the Top 10.
4. Don McLean – Till Tomorrow
“Till Tomorrow” is a soft, emotional goodbye expressed through music. It’s filled with a sense of longing and separation —and all those emotions are paired with beautiful instrumentation in a classic folk style. The guitar is just perfect, and the lyrics are deeply affecting. It’s everything you could ever want from this type of song. This composition, without a doubt, earns its place among Don McLean’s best.
3. Don McLean – And I Love You So
This one’s yet another gem from McLean’s debut album Tapestry. “And I Love You So” is incredibly soft, warm, and beautifully vulnerable song. No wonder it’s been covered by music icons like Elvis and Perry Como. There’s just something truly special about it. Maybe it’s the seeming simplicity of the lyrics, or the honest raw delivery, or the magic guitar. Whatever it is but this one belongs in the TOP 3.
2. Don McLean – American Pie
You can’t talk about Don McLean’s greatest hits without mentioning “American Pie.” This epic 8-minute and 43-second track is a cultural monument that made Don McLean a household name. It was inspired by the tragic plane crash that took the lives of Buddy Holly, Ritchie Valens, and The Big Bopper – an event McLean famously called “the day the music died.” But this song is more than just a tribute. It has incredible lyrics that still spark debates about their deeper meaning to this day.
“American Pie” could easily be McLean’s best song — and for many fans, it is.
1. Don McLean – Vincent
And the first place in the chart goes to “Vincent”. It’s the crown jewel of Don McLean’s discography. Even though “American Pie” is the more popular song, it’s “Starry, starry night” that carries this unmistakable, mystical mood. This is a true masterpiece. It only takes that first line to pull you into one of the most heartfelt tributes ever written about an artist.
“Vincent” was inspired by Vincent van Gogh and was written after McLean read a biography about the painter. But even people who don’t know this backstory still find the lyrics and the song incredibly relatable. Which just goes to show that the best music always reaches our hearts through the sheer power of emotion.
On a side note, I wish this track had been featured in The Holdovers (2023). It would’ve matched the mood and vibe of that wonderful movie so nicely. Just like “Silver Joy” by Damien Jurado and “Crying, Laughing, Loving, Lying” by Labi Siffre. You can find both songs on the Song of the Day page.
TOP 10 Hits Playlist
Here’s a quick sum-up of the entire song list.
🎧 10 Best Don McLean Songs:
- Vincent – from American Pie (1971)
- American Pie – from American Pie (1971)
- And I Love You So – from Tapestry (1970)
- Till Tomorrow – from American Pie (1971)
- Chain Lightning – from Chain Lightning (1978)
- Winter Has Me In Its Grip – from American Pie (1971)
- Crying – from Chain Lightning (1978)
- Sea Man – from Believers (1981)
- Empty Chairs – from American Pie (1971)
- Castles in the Air – from Believers (1981)
Listen to the Don McLean Best Songs playlist on SPOTIFY 🎧
Listen to the Don McLean Best Songs playlist on YouTube 🎧
About Don Mclean
Don McLean (born October 2, 1945) is an American singer-songwriter known for his folk, rock, and country blend. Since childhood he pursued music, influenced by such folk legends as Frank Sinatra and Buddy Holly. He released his debut album Tapestry in 1970.
His second album, American Pie (1971), brought him global fame with its eight-and-a-half-minute title track becoming a cultural phenomenon. This album included another famous hit “Vincent.”
Don Mclean’s discography includes 20 studio albums, four live albums, 11 compilation albums, and 16 singles.
For the latest news from the artist check his website.
