The essential Paul Simon playlist

Paul Simon was the first-ever "sad boy" artist. Before there was Morrissey or Juice Wrld, there was The Sound of Silence, a song about loneliness and humanity's inability to communicate. 60 years later and people are still trying to replicate it. 

As a song about endurance, it's only fitting that The Boxer remains a powerful and gut-punching anthem. The softness of Simon's guitar is attacked by a one-two punch of synth and snare, but like the end of Rocky II, our hero remains standing after a number of crushing blows. 

This optimistic tune about a man who misses his mother was a major hit for Simon in 1971. More importantly, it saw the artist leaving Garfunkel and branching out into new terrain. 

In 1986, Simon set Billboard records with the release of his African single Graceland. The song spent over a month at #1 and has since been hailed as one of the greatest songs ever made. It features one of my favorite choruses, a number of African instruments, and the Everly Brothers on backup. It's a perfect mashup of genres. 

Appearing on Simon & Garfunkel's third record, For Emily, Whenever I May Find Her is a deeper cut that's worth listening to. Especially for fans of poetry... 

Combining the traditional folk ballad Scarborough Fair with lyrics about nature, this is the band's most dreamy number. The song whisks you away to a misty morning where the scent of herbs and flowers linger like memory's sweet perfume. You could swear you lived it, but really you just listened. 

Simon has written a lot of great first lines to his songs, but nothing compares to "When I think back on all the crāp I learned in high school/ It's a wonder I can think at all." Heck, it might be my favorite line in music history. That the rest of this toe-tapping, glissando-shimmering banger is just as good is a testament to Simon's genius. 

Simon & Garfunkel had a serious knack for harmony, and Flowers is proof of that expertise. You can never tell who's singing on this track; their voices are as inseparable as leaves on a clover. 

Written by Simon and released in 1986, You Can Call Me Al is an essential part of the artist's repertoire. In addition to being a #1 hit, the song also has a music video with Chevy Chase that you've seen at least once...or twice...or 20 times. 

I don't know if Robert Frost had a calendar, but if he did it might've looked something like April Come She Will: a collection of poetic insights about each month of the year. The song may not be one of Simon & Garfunkel's greatest hits, but it remains as spry as July. 

In an age of war, crime, protest, and inflation, this state-of-the-union address is more timely than ever. As Simon cuts through the facade of the American Dream, you simply won't be able to listen to it without crying. 

Most artists find a groove and stick with it (Van Morrison, Del Shannon, The Beatles), but Simon loves to keep us on our toes. Just when you settle into a Cuban groove, he cuts to a chorus straight out of a Motown song. 

Speaking of mixing genres, Simon found a way to mix Spanish folk and New York rock on this 1970 classic. The melody has been covered 4,000 times dating back to 1913, but Simon's lyrics are what make this version stand out.

In Only Living Boy in New York, a lonely Simon writes an ode to Garfunkel who's away in Mexico working on a movie. Of course, the movie would eventually lead to their breakup months later, but there's something beautiful about Garfunkel hopping on the chorus to remind Simon that he's still here. 

No song captures the jubilation and heartbreak of love better than this one. One second you feel like you're on top of the world, the next Cecilia is sneaking out your back door. 

A sequel to The Boxer, this is yet another song about a poor boy who goes on a journey far from home, rolls with the punches, and finds love after a lonely struggle. It's Vagabond with a sense of humor, The Grapes of Wrath with sex. It's one of the most beautiful songs ever written. 

I hope you know how to whistle...cause it's impossible not to whistle along to this timeless classic. Every time it comes on at a bar, the entire place turns into a Karaoke machine. 

The title track of Simon & Garfunkel's fourth album, Bridge Over Troubled Water is an ode to the pair's life-long friendship, which was able to produce some of the best music of all time. Need proof? Listen to the song. 

Even though he was only 23 at the time, Simon scored a crossover hit with Mrs. Robinson, a tune that was not only a chart-topper but also the theme song for The Graduate. Even if you haven't seen the movie, you've heard the song. 

We'll send you off on a high note: a groovy track with a light bass, a playful chorus, and one of the finest melodies ever recorded.