The definitive Simon & Garfunkel playlist

We kick off this list with one of the more unique offerings from the legendary duo. "El Cóndor Pasa" is a Peruvian piece created in the early 1900s and meant for an orchestra setting. In the1960s, Andean folk group Los Incas incorporated the piece during a performance in Paris, which reportedly enamored Paul Simon. Simon & Garfunkel covered its version of Los Incas take for the iconic and chart-topping Bridge Over Troubled Water album from 1970. Perhaps it's an acquired listen for some of the duo's more pop-preferring fans, but worth the time, nonetheless.

Simon & Garfunkel's debut album from 1964 was a commercial flop and even saw the two artists temporarily go their separate ways in its wake. However, as we'll see, the album aged better than it was initially received. This title cut of the record is undeniably folksy but with a hint of pop, an indication that Simon & Garfunkel had a sound that was going to be more accessible beyond the prominent folk scene of New York City from the early 1960s.

A deeper cut from the Sounds of Silence (1966) album. "Richard Cory" is based on the late 1890s poem by the same name from Edwin Arlington Robinson. The story of an envious factory worker toward his well-off and presumed happy boss (Cory) offers some dark subject matter for Paul Simon to tackle. This is a wonderful piece in terms of the song's structure, a Dylan-esque vibe, and those legendary Paul Simon/Art Garfunkel harmonies.

By 1968, Simon & Garfunkel saw a rise in popularity and prominence, thanks to the release of albums Sounds of Silence, Parsley, Sage, Rosemary and Thyme, and the duo's presence on The Graduate soundtrack. The success continued with 1968's Bookends record. "At the Zoo" is the closing number on that album and a unique ode to Paul Simon's love for New York City. The track was slated to be included on The Graduate soundtrack but was never part of the album.

Another offering Bookends. On the vinyl version of the album, the dreamy "Old Friends" segues into the "Bookends Theme," which is the longer reprise of the record's 30-second "Bookends" opener. There's an almost orchestral, Rogers-and-Hammerstein feel to "Old Friends," while "Bookends Theme" has enjoyed a lasting legacy among the duo's catalog. Indeed, these are two of Simon & Garfunkel's most poignant songs, and together, the listening experience is more impactful. 

When Paul Simon and Art Garfunkel split after the poor reception of their first album, the former released a collection of songs in the United Kingdom known as The Paul Simon Songbook (1965). "Kathy's Song" was part of the record and was later released on Sounds of Silences. It's undeniably folk but also beautiful, poignant, and inspired by Kathy Chitty, a woman Simon met in England and referred to in numerous S&G tracks. It proved that Simon's songwriting could branch out and display more depth. 

Here we have a tale of young loves hitchhiking together in search of "America." The tune cracked the Billboard Hot 100 for Simon & Garfunkel. However, it also produced many successful cover versions from artists like Yes and Josh Groban. There's a certain level of bombast to the tune, though nothing that would rattle the windows. Still, one of the duo's more boisterous tracks, off Bookends, has enjoyed quite the respectable legacy.

No slight on the studio version of "For Emily, Whenever I May Find Her," released as part of 1966's Parsley, Sage, Rosemary and Thyme. But the live rendition found on the duo's stellar greatest hits collection from 1972 is quite sterling. The acoustically prominent tune is Simon & Garfunkel at their folk best. Poignant lyrics from Paul Simon and a stellar vocal performance from Art Garfunkel. Perhaps his best musical moment during their time together?

The number of iconic musical moments within the Simon & Garfunkel legacy is just one reason the duo enjoys legendary status. Here is another obvious nod to New York City and the venerable Queensboro Bridge, aka "The 59th Street Bridge" song or "Feelin' Groovy." The tune from Parsley, Sage, Rosemary and Thyme might be the epitome of the 1960s folk scene in New York. It's also an example of how it can be marketable and appealing to mass audiences.

"Keep the Customer Satisfied" is notable for the trumpet work that adds an obvious jazz element to the piece. While the tune was a top-40 hit for Gary Puckett & The Union Gap in 1971, it's considered an overlooked and underrated song from Bridge Over Troubled Water. With a catalog as popular and iconic as Simon & Garfunkel's, various songs might slip through the cracks regarding commercial accessibility. Consider this an example of that but still well worthy of celebration.

Another special Simon & Garfunkel moment, "Homeward Bound" first appeared on the United Kingdom version of Sounds of Silence. In the United States, it came out on Parsley, Sage, Rosemary and Thyme and became one of its more successful songs. "Homeward Bound," which includes more roundabout references to Kathy Chitty, was a top-10 hit in the U.K. and reached No. 5 on Billboard's Hot 100. A brilliant live version of the tune can be found on Simon and Garfunkel's Greatest Hits.

Two years before it was part of Bookends, "A Hazy Shade of Winter" was released as a single. It was a top-15 hit for Simon & Garfunkel and one of the duo's more "fast-paced" tunes. Though, plenty of folk sensibility still catered to all fans, regardless of musical preference. Fast forward more than 20 years, and Gen-X listeners massively embraced an even more up-tempo and somewhat edgier version from all-girl rockers The Bangles. That version, from the Less Than Zero soundtrack, reached No. 2 on Billboard's Hot 100.

It's always a good time when artists include the title of an album within the lyrics of a song with a different name. Here we go with "Scarborough Fair/Canticle," a traditional English ballad that was made relevant in the modern day because of Simon & Garfunkel. The "Canticle" portion of this listening experience was built out of a Paul Simon anti-war song, "The Side of a Hill," from 1963. Together as one, the piece reached No. 11 on the Hot 100.

Originally part of The Paul Simon Songbook, "April Come She Will" later found a home on Sounds of Silence, even as the B-side to "Scarborough/Canticle." It became one of Simon & Garfunkel's most beloved songs, though perhaps lagging in popularity within the confines of the duo's musical arsenal. It's another example of how Simon's songwriting expanded — notably from the point of creativity. The song uses the changing seasons to chronicle the changing moods of a girl.

Another piece from The Paul Simon Songbook, "I Am a Rock" was initially released as an acoustic track, but the spruced-up, electric version from Sounds of Silence is perhaps the way most casual folk/pop rock fans relate to this tune. This is one of Simon & Garfunkel's most recognizable songs yet tends to be overshadowed by some of their more popular tunes. A song of emotional isolation, "I Am a Rock" can stand toe-to-toe with anything else in the duo's legendary catalog.

The easiest way to describe "Cecilia" is fun. Reportedly, the song's genesis happened at a party, so the entire vibe of the tune makes sense. It's a rollicking good time for the ears and one of the band's most upbeat and well-known songs. It's managed to span generations. Another special moment from Bridge over Trouble Water, "Cecilia" peaked at No. 4 on Billboard's Hot 100.

"Mrs. Robinson" can be found on various Simon & Garfunkel releases, notably Bookends and an EP by the same name. However, it's probably best known for its inclusion in The Graduate. Paul Simon wrote it for the film, and shorter versions of the song appear in the iconic Mike Nichols film that helped bring the duo's music to the masses on a more significant level. "Mrs. Robinson" was the second Simon & Garfunkel song to hit No. 1 on the Hot 100 and won the Grammy for Record of the Year in 1968. Meanwhile, Frank Sinatra and The Lemonheads each put out successful versions of the classic.

At this point in our list, the top five Simon & Garfunkel songs are relatively interchangeable. This five-time Grammy-winning song is considered one of the greatest pop offerings of all time. Though, there is a gospel vibe to this beautifully composed and executed track. With Art Garfunkel on lead vocals, the title track to the duo's fifth and final studio album sat atop the Billboard Hot 100 for a six weeks. 

Sticking with the Bridge Over Troubled Water record, "The Boxer" is one of Simon & Garfunkel's most iconic tunes — a top-10 hit. However, in some ways, it's overshadowed by the title cut when picking the best song on the album. "The Boxer" has plenty of autobiographical undertones for Simon, whose career seemed to generate as much criticism as it did praise. The track was a metaphor for the famed artist. 

The journey "The Sound of Silence" took to becoming one of the great folk-rock songs in music history is quite interesting. It was the song that got the duo a record deal in the first place and released, in its original acoustic form, on its unsuccessful debut Wednesday Morning, 3 A.M. Then, in 1965, the track was redubbed, unknown to the pair, with a more plugged-in punch and reached the top of the Billboard Hot 100. Thus, bringing Paul Simon and Art Garfunkel back together to build on the success of the remix, record their 1966 follow-up album Sounds of Silence, and go forth on what would be a relatively brief but Hall of Fame career together.