It wasn't clear at the time, but Bridge Over Troubled Water was an album about the end — a casually ambitious look back at an expiring musical partnership (Simon and Garfunkel) and decade (the Sixties). Recorded in late 1969, it's largely remembered for a pair of big-themed production masterworks: "The Boxer" and "Bridge Over Troubled Water," led by Paul Simon and Art Garfunkel, respectively. "Bridge" quickly attained the beloved stature of a hymn, while "The Boxer" — a metaphor for the immigrant experience in America — ranks with Simon's finest songs. At the other extreme are sprightly tunes that hearken back to the duo's Fifties roots: "Cecelia," whose echoed hand claps sound like an early hip-hop drum loop, and "Keep the Customer Satisfied," the antic tale of a flimflam man staying ahead of the law. During the Bridge sessions, Garfunkel was often working on the film Catch-22 in Mexico; Simon gently notes his absence in "The Only Living Boy in New York." The notion of life chapters closing also permeates the folksy bossa nova "So Long, Frank Lloyd Wright." It's ironic that "Bridge Over Troubled Water," a gospel-style song of reassurance and solidarity that Simon wrote as a vehicle for Garfunkel's golden tenor, would be one of their final collaborations. But they exited on an exhilarating note.

“He Will Break Your Heart”

A lightly swinging Latin-influenced, almost cha-cha groove and close harmonies decorated Jerry Butler's early soul hit "He Will Break Your Heart," delivering a stately warning that his rival would never love his girl like he did. The melody came to Butler as he was driving on the highway from Atlantic City, New Jersey, to Philadelphia with Curtis Mayfield, and as Butler told Rolling Stone, "I just sang the melody and Curtis put the chords to it." The song's premise, Butler added, "was something that I'd lived ...The lyric was an experience rather than a revelation. Whereas music is usually a revelation."