The cover of Harry Nilsson’s most critically acclaimed album, 1971’s Nilsson Schmilsson, shows a disheveled Nilsson wearing a robe, one hand in his pocket and the other holding a hash pipe. The album title and cover are perfect illustrations of the humor and apathy that encompassed Nilsson’s musical career. Noel Murray of the A.V. Club wrote of Nilsson: “Nilsson became the musician’s musician, admired for his wild arrangements, his insistence on satisfying his own muse before making his record label happy, and his willingness to mock himself, the culture, and every notion of showbiz propriety.â€
Harry Nilsson liked nonsense. Though two of his most famous tracks, “Everybody’s Talkin†and “Without You,†are somber in tone, they aren’t emblematic of his career nor are they songs he wrote. It’s not that Nilsson didn’t compose heartfelt songs, but so much of what actually represents Harry Nilsson is the nonsense, the humor, the randomness in his writing and performing.
Nilsson was famously close with John Lennon, Ringo Starr, The Monkees, and various other mainstream musicians of the ‘60s and ‘70s. But he never became the household name his contemporaries did—likely because of his erratic lifestyle (see his Lost Weekend with John Lennon) and increasing refusal to do something simply for commercial accessibility.
One constant in Nilsson’s music was his humor – the subtle deadpan, blatant belligerence, and random wordplay in his records. His comedy may not have rivaled a Carlin or Pryor standup set, but for someone as proficient in music as Nilsson, it was a useful weapon in his arsenal. Musicians like Nilsson, Warren Zevon, and Randy Newman used satire and irony to assuage their somber side – like good comic relief in drama.
Nilsson could write a song about his father abandoning him as a child (“1941â€); he could capture the sorrow of isolation (“Oneâ€) and he could make a musical comedy called the Son of Dracula starring himself as Count Downe and Ringo Starr as Merlin.
There are plenty of songs and outtakes from Nilsson’s career worth giving a listen.  Here are some of the comedic compositions that make Nilsson such a standout of his era:
Good Old Desk
“Good Old Desk†has a whimsical melody and the subject matter is light; the narrator considers his desk a reliable companion, there for him 9-5 to keep his “hopes alive.†He really loves this desk, so much that the song ends with the narrator opening one of the drawers and finding a picture of him working at that same beloved desk.
Like many comedians, Nilsson inserted his beliefs in his humor. He discussed the meaning of the song when he appeared on Playboy After Dark:
“It’s not really so much about a desk as it is an anagram game.†Nilsson told Hugh Hefner it had to with man’s modern concept of a higher power. Good Old Desk = G.O.D. Nilsson later claimed he was kidding about this reference, but his fans and contemporaries believe this was Nilsson’s way of grappling with the concept of a higher power.
The Point!
Nilsson devoted an entire album to a pun. The Point! is either completely nonsensical, a random story about people with points on their heads or it’s an existentialist statement on how society judges each other and themselves.
The album tells the story of a town, the Land of Point, in which everything, the people, the animals, the objects all have a literal point coming out of them. They use their points for games and identifying and accepting one another. One child, Oblio, does not have a point. Oblio is an outcast because he has no point, literally and figuratively.
There is a pointless forest where “all things are pointless and nothing is pointed.†Characters include: the Fat Sisters and the Pointed Man who says “A point in every direction is the same as no point at all.â€
How did Nilsson think of the idea? He was inspired to write the story when tripping on acid in a forest.
Coconut
If you’ve seen Reservoir Dogs, then you’ve heard this song. It’s a perfect track to follow a Mexican Standoff.
“Coconut†is a novelty song; it’s all nonsense. If there’s any comedy to be mined from the lyrics it’s the lack of awareness from the woman and doctor characters. The woman asks for help from a doctor who prescribes the exact same treatment that made the woman sick in the first place, putting a lime in a coconut and drinking it.
At the recommendation of his producer, Richard Perry, Nilsson did the character voices for the song—so he used some type of Jamaican accent for the doctor.
I’d Rather Be Dead
This darkly comedic song describes the narrator’s preference to be dead rather than live in old age, unable to take care of himself. It’s not really a comical concept at face value, but the cheery melody, and vocal style create the comedy.
The song was recorded in a nursing home with a group of elderly folks singing the chorus with Nilsson. It seems both cruel and oddly optimistic that Nilsson got them to sing about this subject with him.
Joy
“Joy†is a country music parody. It sounds like a country standard with Nilsson tweaks. It’s not an inherently funny to song to start, except that he’s mocking and paying homage to the country genre simultaneously. He begins to add his subtle deadpan humor into the song:
The other day I met a girl named JoyÂ
She said, “Roy, I’m gonna make you my joy boyâ€
Well, she took me for a ride, sort of a joy rideâ€
The way he sings the last line is as if he knows it’s ridiculous.
By the end of the song he starts repeating lines things went good, things went bad, things went good, they went bad, good, bad, good, bad. He gets faster and faster and then trails off singing good, bad, good, bad as if he’s a frustrated child who doesn’t know how else to express himself.
You’re Breaking My Heart
Instead of writing a ballad about heartbreak and loss, Nilsson sings:
You’re breakin’ my heart
You’re tearing it apart
So fuck you
This is the blatant belligerence mentioned earlier. Nilsson uses electric guitars, horns, and expletives to express his anger. The deliberate lack of metaphor makes a song about suffering into a joke. It’s one of the few breakup songs that’s so straightforward in it’s message.
This track appears on Son of Schmilsson, the follow up to Nilsson Schmilsson. The album is a personal favorite and a good representation of just how much Nilsson did what he wanted to at this stage of his career. The outtakes basically become the tracks on this album. It also features one of his best song titles: “The Most Beautiful World in the World.â€