***REVISIONS: I added on to the analysis of Songs 1, 2, 3, and 4. I eliminated songs 5 and 6, adding a Dylan track and Drive-By Truckers tune.

The Big Lebowski revolves around a case of mistaken identity between Jeff "the Dude" Lebowski and Jeffrey Lebowski (the Big Lebowski). The Dude is the ultimate unemployed L.A. slacker who leads a simple life and enjoys the simple pleasures in life; then his house is broken into, leading him on an adventure to unravel a mysterious kidnapping. This disrupts his usual routine of getting high and bowling.

The Dude is a sort of counter culture roll model. He is still living his life like it were the 60's, but without his protesting. He does what he wants and does not bother himself with the normal details of life. Understanding how one manages to live his lifestyle is incredible perplexing. The Stranger puts it best, "The Dude abides. I don't know about you but I take comfort in that. It's good knowin' he's out there. The Dude. Takin' 'er easy for all us sinners."

PLAYLIST

Song 1:

Kenny Rogers - Just Dropped In (To See What Condition My Condition Was In)

I woke up this mornin' with the sundown shinin' in
I found my mind in a brown paper bag within
I tripped on a cloud and fell-a eight miles high
I tore my mind on a jagged sky
I just dropped in to see what condition my condition was in...

Someone painted "April Fool" in big black letters on a "Dead End" sign

This song is representative of some of the dreams and acid flashbacks that The Dude experiences. He goes through these whacky dream sequences, which entail bowling shoes piled as high as the eye can see and floating down bowling lanes in the sky. The song is meant to reflect the LSD experience and it really does justice to The Dude's own dream/flashback sequences. It's psychedelic feel allows us to get a sense of that aspect of The Dude's life.
The 'april fool' line is symbolic of how the other characters who did not know The Dude had him pegged as a dupe. They underestimated who The Dude was and what he was capable of accomplishing.

Song 2:

Oasis - Roll With It

You gotta roll with it
You gotta take your time
You gotta say what you say
Don't let anybody get in your way

The Dude is incredibly laid back, and does not let most things affect him. He doesn't mind being poor and jobless (in fact it seems he would rather have it be that way), but when The Big Lebowski tries to pull a fast one on him he does not stand for it. Once he realizes that he's been duped he goes straight over to Lebowski's and tells him exactly what's on his mind, and then just rolls with the punches and moves on with his life. This song has a very easy going feel to it with a nice smooth flow, similar to the demeanor of The Dude.

Song 3:

Eagles - Take It Easy

Well, i'm running down the road
Tryin' to loosen my load
I've got seven women on
My mind,
Four that wanna own me,
Two that wanna stone me,
One says she's a friend of mine
Take it easy, take it easy
Don't let the sound of your own wheels
Drive you crazy
Lighten up while you still can
Don't even try to understand
Just find a place to make your stand
And take it easy

After The Dude becomes involved with the kidnapping it seems that everyone in town is after him. He is constantly being mistaken for the Big Lebowski and having people come after him for money (which he doesn't have). This song talks about the women coming after the speaker for various reasons, and aside from the gender it is very similar to the perdicament The Dude found himself in. He had a porn king and his henchmen/actors coming after him for money that the Big Lebowski's wife owed; he had the three nihilists coming after him for the ransom money; he had the Big Lebowski coming after him for the money that he suposedly gave The Dude; and he had his buddy Walter latching on to him and screwing everything up. When all he wanted to do was "take it easy" and maybe do a little bowling. This is a very melodic song with a very laid back feel to it, which is similar to the way The Dude kind of keeps his laid-back demeanor throughout the movie despite being in tough and stressful situations; however, this is not to say that The Dude does not get worried, but rather that he seems calm on the outside and keeps his typical demeanor.

Song 4:

Elvis Presley - Blue Suede Shoes

You can burn my house,
Steal my car,
Drink my liquor
From an old fruitjar.

Do anything that you want to do, but uh-uh,
Honey, lay off of my shoes

The way The Dude gets mixed up in the whole kidnapping ordeal is because "a Chinaman peed on [his] rug" thinking it was the Big Lebowski's. Throughout the movie he talks about how "the rug really tied the room together", mainly because it was the only thing worth value, at least to him, in his house. He didn't care when his buddy Walter made him crash his car, and when his car was stolen he only cared about his Creedance tapes. There are few things that The Dude cares about and holds dear to his heart, and he wants people to just "lay off" that stuff. And throughout the movie he has his Creedence tapes messed with, his rug stolen and peed on, and his bowling ball slammed into the ground.
This has a very old school rock feel to it. Elvis and The Dude share some similarities, in they were both out of place in their times; however, Elvis came before his time and then faded into his time, while The Dude began in his time and the time faded away from him.

Song 5:

Easy On Youself - Drive-By Truckers

You got it down, you been around
and you won't change your life...

Ten years down the road you'll find you're left behind. You're left behind...

Don't be so easy on yourself
'cause this one might be all that you have left.
Rearrange the voices in your head and remember what they said.
Don't be so easy on yourself.

This song tells the story of the flaw of The Dude. He is the tragic hero of the story; tragic because he allows the situation to blow up, nearly out of his control, due to his lack of assertiveness. He allows Walter, and many others, to push him around and have him play their game.
It also shows how everything around him is changing and he resisting them. Bowling is a prime example of this resistance to change. The popularity of bowling peaked in the late 50's and early 60's, but The Dude refuses to acknowledge that. He is stuck in the 60's mindset, while everyone else is living in the early 90's. He is a very trusting and relaxed person, something that allows him to be taken advantage of by others. This is something that he realizes over the course of the movie. In turn, he decides to solve the mystery and prove to everyone that he is no dupe, but rather that he chooses to live his life the way he does.

Song 6:

Jimmy Buffet - I don't know and I don't care

Why does the sun set in the west
and why does my heart keep beating in my chest
what ever happened to the Duke of Earl
I gotta PBS mind in an MTV world

Is it ignorance or apathy
I forget these lessons taught to me
Some say life isn't fair
hey I don't know and I don't care

Ambivalent, well yes and no

....

Therapy is extremely popular
popin' bubble wrap is radically cheap
you choose which one helps with your problem
I'm gonna get some sleep
I'm gonna get some sleep

The Dude did not want to be bothered with the whole kidnapping scheme, but he was brought into it. When he finds out it was fake he went and said his piece to the Big Lebowski and walked out of the room as the Big Lebowski was trying to explain it and critique The Dude. He didn't care what the Big Lebowski had to say to him. The Dude just wanted "to go bowling" which is to him the same thing that getting "some sleep" is to the speaker in this song. neither one of them care to spend their time dealing with questions that don't have answers or things that can't be resolved.

Song 7:

Bob Dylan - The Man in Me

The man in me will do nearly any task,
And as for compensation, there's little he would ask...

Storm clouds are raging all around my door,
I think to myself I might not take it any more...

The man in me will hide sometimes to keep from bein' seen,
But that's just because he doesn't want to turn into some machine...

This is representative of The Dude's struggles throughout the film. He is abruptly thrown into the center this whirlwind of inter-related events, which temporarily turn his life upside down. The Dude rises to these challenges and perseveres. His dealings with these events come somewhat as a surprise to the audience and many of the other characters. He is seen as a lazy dupe by most, and idolized by his friends for his passive laid-back nature. However, he is the one to solve these mysteries. 'The man in [him]' took over and proved just what he was capable of doing. This is one of the most serious song on the playlist, and has the most somber tone. The tone is a good fit for representing this serious part of The Dude's life.

Song 8:

Arrogant Worms - Let's Go Bowling

Well grab your shoes, and grab your balls
And lets head to those heavenly halls
Sit on down and grab a beer
Because bowling time is pretty near
Tortured men forget their pain
When they head to the bowling lane

It seems fitting to finish this playlist the way the movie finishes, with bowling. This is also symbolic of the role that bowling plays in his life, there is no problem in his life that bowling can't fix. It is where he feels relaxed and at home, and where he can "forget [his] pain." His life revolves around "bowling time" and it seems that everything else in his life is just filler between rounds.