“Street Hassle”

Length: 11:00

Artist: Lou Reed

Album: Street Hassle

Released: February, 1978

“Street Hassle” is without a doubt the standout track on the album that bears its name, and perhaps one of Lou Reed’s best, period. It is split into three distinct parts that tell three different stories. The first is about a woman picking up a male prostitute, the second a drug dealer recounting the death of a woman who overdosed in his apartment, and the third a verse from Reed about love and loss. The song feels more like spoken word with strings and guitars reverberating in the background than a conventional song. As a bonus, Bruce Springsteen delivers a short, un-credited verse around the nine-minute mark.

“Impossible Soul”

Length: 25:34

Artist: Sufjan Stevens 

Album: The Age of Adz

Released: October 12, 2010

At over 25 minutes in length, “Impossible Soul” could practically be an album by itself—or at least an EP. It closes out an album that marked a big change in Stevens’ career—a shift away from a more traditional folk sound towards music grounded in synths and electronics. The track has five distinct parts that cover a wide range of styles and emotions, including quiet guitar picking, a call-and-response sing-along, and even a dance breakdown. Its runtime is fairly daunting, but if you have the time, “Impossible Soul” offers a rewarding way to spend a half hour.

“The Battle of Hampton Roads”

Length: 14:10

Artist: Titus Andronicus 

Album: The Monitor 

Released: March 9, 2010

A Civil War concept album seems like a ludicrous idea when you first hear it, but Titus Andronicus managed to execute it to near perfection. “The Battle of Hampton Roads” is a perfect microcosm of The Monitor—which gets its name from the Union warship used at Hampton Roads—as a whole. It features manic lyricism that deals with anxiety, suicidal thoughts, fantasies of revenge, and more. All of this gets laid overtop of punk-inspired Irish jigs, bagpipes, and buzzing guitars. Suffice it to say there is a lot going on in this song, but it adds up into something cathartic, and is a perfect way to end the album.

“Sing About Me, I’m Dying of Thirst”

Length: 12:41

Artist: Kendrick Lamar 

Album: Good Kid M.A.A.D. City

Released: October 22, 2012

Most rappers would likely have trouble finding enough to say to make a solid 12-minute song, but as is clear from the album as a whole, Kendrick Lamar is not short on inspiration or ideas. “Sing About Me, I’m Dying of Thirst” is a beautiful, empathetic song that tells the story of two peripheral characters in the world Kendrick describes in GKMC. The first two verses are told from the perspective of these two characters, before Kendrick offers his own view in the third, rapping about death, vengeance, sin, and salvation. My only complaint is that it is a track that demands multiple listens—a somewhat tall order for a song with a double-digit run-time.