The 5 Best Paul Simon Songs of the 2000s

Paul Simon seems to respond to each era with a batch of songs that are tailor-made for the times. That hasn’t stopped since the turn of the millennium, even if his new releases don’t get as much publicity as they once did.

To prove just how effective he’s been over the past few decades, we singled out a song from each of the five studio albums he’s released since 2000. And they’re every bit as profound and moving as any work he’s ever done.

“Darling Lorraine” from You’re the One (2000)

You’re the One was Simon’s first studio album in a decade, as he had spent much of the ’90s working on the musical The Capeman. As such, the album betrays a little rust, and the production is a little less engaging and warm than we’re used to from Simon. But “Darling Lorraine” is indubitably a winner. Simon tracks a relationship from its inception to its collapse, with the musical moods seeming to change in accordance with the rollercoaster ride the narrator endures. That Simon dares to take the song to some difficult places is a testament to his honesty and fearlessness.

“Another Galaxy” from Surprise (2006)

Simon brought the legendary knob-twiddler Brian Eno into the making of Surprise as a kind of unofficial collaborator. The influence can be felt in the way the songs flirt with electronic textures. But Simon didn’t come off like someone who was a dilettante in that modern arena. Instead, he matched his storytelling to the new sounds quite seamlessly, and “Another Galaxy” is the apotheosis of those efforts. A moving story about a girl who dares to live a life other than the one laid out in front of her, the song uses the atmospheric effects to represent the road less traveled she decides to take.

“Rewrite” from So Beautiful or So What (2011)

So Beautiful or So What is Simon’s best album of the 21st century, better than anything really since Graceland. The entire album is suffused with grace, wisdom, and humor, and “Rewrite” is the stunning centerpiece. Just the music alone soars with incredible work from Bakithi Kumalo on bass and Vincent Nguini on guitar, creating a leisurely yet transformative atmosphere. When you dive into the song’s lyrics, it only gets more impressive. Simon creates an utterly moving character sketch of a guy whom society’s left behind, but still refuses to stop loving and caring for others.

“Wristband” from Stranger to Stranger (2016)

Going all the way back to “Cecilia,” Simon’s ability to create an invigorating rhythmic bed for his songs has been just as important as his words and melodies. That’s evident on this banger from Stranger to Stranger, an album which continued his stretch of late-period excellence. As a listener, you get launched forward into this song, and once you’re in there, you won’t want the ride to end. The song also shows off Simon’s sense of humor, as he imagines a scenario where he gets locked out of his own concert. That thought that sends him off into more serious ruminations on people undeservedly getting shut out of life’s pleasures.

“The Sacred Harp” from Seven Psalms (2023)

Ever the restless seeker, Simon continues to find ways to expand his artistic horizons. In 2023, despite dealing with hearing problems, he delivered Seven Psalms. It’s sort of one long piece divided into several sections, so technically “The Sacred Harp” isn’t listed as an individual song. Nonetheless, it’s perhaps the prettiest piece of individual music, which is saying something because the entire album is quite lovely. Simon gets help from his wife Edie Brickell on vocals for a story about a couple who run across a pair of semi-mystical travelers. The piece mixes the divine with the mundane in magical ways.

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