It’s far too much fun to find songs about sex, and sometimes it’s a bit too easy. There are the obvious culprits: George Michael’s entire Faith album deals with relationships and sex, Two Live Crew did quite a few lewd numbers about fornication, and AC/DC’s “You Shook Me” is a favorite of sex-crazed teens (and these days, many of their parents, too).

But I wanted to shake that up a bit: throw in a few obvious ones, as well as some songs that are a bit more obscure, or those performed by songwriters not known for writing sexually-charged songs. They’re the songs that would have Salvador Dali saying “oooOOOooo!” (Hat tip to Craig Ferguson for that riff.)

1. “Sit On My Face” - Monty Python (from Monty Python Sings!)
   Obvious? Oh yes, but it’s quite blatant about it’s intent: let’s get down, do some 69, and sound like a proper army regiment as we do it. Hmmm….
2. “Duncan” - Paul Simon (from Paul Simon)
   I was telling sprite as I ws prepping this list that I didn’t think that Paul Simon had a sex song in his catalog. However, he had two: “Cecilia” and this song, “Duncan,” which talks about a sexual encounter that, in modern interpretation, could swing either way. “She took me to the woods/Saying here comes something and it feels so good/And just like a dog I was befriended/I was befriended” - you make the call!
3. “Iowa” - Dar Williams (from Out There Live)
   Dar often introduces this song (her most overt sing-along at most shows) by citing its inspiration in the “bosomy” hills of Iowa. And the song mentions how these hills make Ms. Williams wish she “had a way with women.” Can’t argue with that, right?
4. “The Town Crotch” - Jonathan Coulton (from Thing A Week Three)
   Every town/neighborhood/school/building has one of these.
5. “Ice Cream Man” - Tom Waits (from The Early Years - Volume 1)
   The “ice cream” served by this guy is not something you’d want to serve your innocent children.
6. “Rudebox” - Robbie Williams (from Rudebox)
   It’s Robbie Williams - no relation to Dar, and certainly a bit more overt in his sexual mischievousness - who is shaking his “rudebox” and rhyming “Durex” with “sex.” That’s fitting, as condoms and sex go together like…. Robbie Williams and having a career that’s successful everywhere except the United States.
7. “Add It Up” - Violent Femmes (from Add It Up (1981-1993))
   The Violent Femmes’ ode to nerdy teenage lust is perfectly delivered in this live performance in front of nerdy teenage fans - what’s not to like?

Download: “Sit On My Face” - Monty Python (mp3)
(Right-click/control-click link to download)

Download: “Duncan” - Paul Simon (mp3)
(Right-click/control-click link to download)

Download: “Iowa” - Dar Williams (mp3)
(Right-click/control-click link to download)

Download: “The Town Crotch” - Jonathan Coulton (mp3)
(Right-click/control-click link to download)

Download: “Ice Cream Man” - Tom Waits (mp3)
(Right-click/control-click link to download)

Download: “Rudebox” - Robbie Williams (mp3)
(Right-click/control-click link to download)

Download: “Add It Up” - Violent Femmes (mp3)
(Right-click/control-click link to download)

Download all the songs in a handy ZIP file:

Download: “Ooooooh!” (ZIP)
(Right-click/control-click link to download)

I guess there’s not a lot to say about these, the idea is they tell their own story. But as David Clennon stressed in “From The Earth To The Moon”, it’s all about context. And it is that which I propose to give you a lesson in… right now:

1. Pink Floyd, “When The Tigers Broke Free”
This is from the film version of “Pink Floyd: The Wall”, and does not appear in any version on the album or many and varied live performances of said work. I can only think that this song - a poetic and visceral summing up of the circumstances surrounding Roger Waters’ father’s death in World War II - is just too personal and soul-rending for the Floyd frontman to want to dilute through casual repetition. Understandable, since his father’s death is clearly, along with the mental self-destruction of Roger “Syd” Barrett, a formative experience in Waters’ life and in one way or another the subject matter of almost everything he’s ever written. I find this scathing indictment of the professional detachment of those planning war, and the personal cost exacted upon those waging it, quite moving every time I hear it.

2. Johnny Cash, “Casey Jones”
Another tragic and honorable sacrifice rendered in classic Americana style, this is the story of the very real John Luther “Casey” Jones and one fateful night in 1900 in Mississippi.

3. Christine Lavin, “The Wild Blue”
Long and rambling and a bit forced and awkward at times, this nonetheless manages to be an emotionally enthralling tale of the origins of the Japanese World War II kamikaze, and the personal toll it took on all involved. It’s rare that I feel that I actually learned something new and interesting from a song, but this is a clear example.

4. Jonathan Coulton, “Kenesaw Mountain Landis”
Shifting gears into the absurd and humorous, we get this slightly exaggerated retelling of the 1919 Black Sox scandal, embellished just a bit here and there by Coulton, who enjoys mining that grey area between the works of Robert Allen Zimmerman and Alfred Matthew Yankovic. This is a stellar example of Maxwell Scott’s adage that “when the legend becomes fact, print the legend”. Make sure you stay tuned for the end of the song where it suddenly takes a hilarious left turn into modern pop rock culture.

5. Bob Dylan, “Billy (part 4)”
This is from the aforementioned Zimmerman’s collection of songs written for the 1973 film “Pat Garrett And Billy The Kid”, Sam Peckinpah’s post-modern revisionist history of the last days of Henry McCarty and the man who knew him well enough to kill him.

6. James Brown, “King Heroin”
Believe me, I wish this wasn’t a true story - but unfortunately Brown knew all too well the power and influence of this immigrant from the Far East. There have been far too many songs written about this opioid and the crafty precision with which it seems to seek and destroy our best and brightest, but no others have personalized the battle by casting the adversary as an actual sentient entity. And here’s where I unfortunately know too much about the subject matter, as I watched this evil seductive being insinuate itself into the lives of far too many people close to me. Unlike some of the previous songs on this list, James is not exaggerating or embellishing one bit. He recorded this back in 1974, long before the “27 List” claimed a few more famous victims. Unfortunately it seems that this King’s reign will persist long past that of this Godfather.

Download: Pink Floyd, “When The Tigers Broke Free” (mp3)
(Right-click/control-click link to download)

Download: Johnny Cash, “Casey Jones” (mp3)
(Right-click/control-click link to download)

Download: Christine Lavin, “The Wild Blue” (mp3)
(Right-click/control-click link to download)

Download: Jonathan Coulton, “Kenesaw Mountain Landis” (mp3)
(Right-click/control-click link to download)

Download: Bob Dylan, “Billy (part 4)” (mp3)
(Right-click/control-click link to download)

Download: James Brown, “King Heroin” (mp3)
(Right-click/control-click link to download)

Songs about madness seemed to be a big deal in the late-1960s, and most of my playlist originates from that era. The rise of psychedelic drugs - and the resulting psychoanalytic push - acted as a muse for many songwriters to document the ordeals of mental instability.

Since I wrote the intro to this month’s selection, I’ll let the songs do the rest of the talking - have fun!

1. “Helter Skelter” - The Beatles (from The Beatles [a.k.a. The White Album])
   This song ostensibly is Paul McCartney’s answer to The Who’s claim as “loudest rock back of 1968.” Fair enough. But it’s also a song that supposedly spoke to Charles Manson, who kept muttering “helter skelter” and citing The White Album as inspiration for his murder spree. All this from a song about a playground….
2. “The Real Me” - The Who (from Quadrophenia)
   Sure, most people cite Tommy as The Who’s rock opera, but as a coherent work, Quadrophenia works much better. The story centers around a protagonist who has a four-sided personality - “quadrophenia” - and the song cycle has four distinct musical themes. This song sets up the original question that the main character puts to his psychologist: “can you see the real me?” Without this album, I doubt that Pink Floyd’s The Wall would’ve been quite as operatic (e.g. musical themes that recur throughout the album).
3. “Knocking ‘Round The Zoo” - James Taylor (from James Taylor)
   Welcome to the early James Taylor. Before he was the laid-back, lanky, cool cat of the adult contemporary set, he was a young, hip, singer-songwriter with a nasty double-whammy case of bipolar disorder and heroin addiction. More than once, he found himself checked into mental hospitals, and this song documents one of those visits. For all the upbeat music that this song has, its lyrics are quite dire. It’s amazing that this young musical talent was one of the first signees to The Beatles’ Apple Records label (though JT’s commercial success was only realized once he moved to Warner Brothers for his second album). The “Kootch” he mentions during one of the refrains is Danny “Kootch” Kortchmar, one of JT’s long-time musical partners.
4. “Help, I’m A Rock” - Frank Zappa & The Mothers of Invention (from Freak Out!)
   Leave it to good ‘ol Zappa, the antithesis of the late-60s drug culture (he never partook of anything hard back in the day), to come up with this crazy song. It’s a reaction to all of the whacked-out psychedelia that took over the rock world in 1966, and seems to sum up the mania that could be induced from listening to the chemical strangeness with a sober mind.
5. “Lithium” - Nirvana (from From The Muddy Banks Of The Wabash)
   Kurt Cobain was a depressed and confused man. Lithium was but one drug prescribed to help him find some happiness in life. Obviously, it failed to exorcise his demons.
6. “Tom Cruise Crazy” - Jonathan Coulton (from Thing A Week 3)
   Want some modern-day crazy? Tom Cruise has it in spades - and Jonathan Coulton is quite happy to sing about it.
7. “Dark Globe” - Syd Barrett (from The Madcap Laughs)
   Rather than look at the post-Barrett Floyd, I decided to go to the source. This song, from Barrett’s first solo album, is a plea for help from a man whose world is crumbling around him. This is a poetic illustration of schizophrenia, penned and performed by a person deep in the throes of his own psychotic breakdown. A haunting close to this disturbing setlist.

Download: “Helter Skelter” - The Beatles (mp3)
(Right-click/control-click link to download)

Download: “The Real Me” - The Who (mp3)
(Right-click/control-click link to download)

Download: “Knocking ‘Round The Zoo” - James Taylor (mp3)
(Right-click/control-click link to download)

Download: “Help, I’m A Rock” - Frank Zappa & The Mothers of Invention (mp3)
(Right-click/control-click link to download)

Download: “Lithium” - Nirvana (mp3)
(Right-click/control-click link to download)

Download: “Tom Cruise Crazy” - Jonathan Coulton (mp3)
(Right-click/control-click link to download)

Download: “Dark Globe” - Syd Barrett (mp3)
(Right-click/control-click link to download)