I think this song, though it may be a reference to being a musician/jazzman, in a larger sense is about following your dreams ("already bought the dream") and being comfortable with the reality you've created for yourself even if it's sometimes dark, languid or bittersweet. Ultimately it's about living the life you choose and accepting that your choices may not resonate with everyone as long as they resonate with you. So yes, it's about freedom. Beautiful.

Wonderful song and an excellent thread of discussions on the meaning. This is definitely one of my favourite songs.

I think the song alludes to a dream of leading a bohemian life. Its a dream that the protagonist has long wanted to pursue and came close to it a couple of times ("I'll make it this time ,I'm ready to cross that fine line ") but probably went back owing to the negative connotations (loser , bummer) that the society in general has of such a life. The 9 to 5 job doesn't excite him any more and he finds it ironic that he has chosen to lead a life which he probably looked down upon earlier from the safety of his glass-covered office ("It seems like only yesterday/I gazed through the glass /At ramblers /Wild gamblers /That's all in the past" ).
But this time he is sure about his choice and he's invested his life and career in his dream ("This one's for real /I already bought the dream") . He knows that the bohemian life is going to be tough. Scorn from the society , penury etc. He knows his true worth in the material world and believes that he can earn many dollars there but he can't buy the true awakening of his soul, the burning desire to do what he wants to do breaking away from the shackles of the stereotyped expectations that socitey has of him. His allusion to learning sax is probably a reason for a defence to his need for earning money in this new life. He surely does not care about the sobriquet of a "loser" and if his family finds it difficult to call him such he suggests that they can give it a glorifed name, Deacon Blues and then will not find it difficult to explain to the outside world.

In summary its a song about the pursuit of a modern person's desire to know himself and his soul and the narration is a kind of defense to all the problems that his critics are pointing out.

I can truly relate to this song. It's essentially about a guy who wants to escape his mundane life.

Great song, great thread. It seemed to me that this is about someone coming to terms with themself as a person that is tragically flawed and can't help it. So he enjoys it as long as he can until he dies behind the wheel.

@"The Dog That Ate": hit it dead on...as if "working" a saxophone isn't enough of a giveaway that this guy is a legend in his own mind, then there's the follow-up: "I play just what I feel." Does it get more trite?

If ever a Steely Dan song wasn't ironic, I have yet to hear it. And Fagen is fond of unreliable narrators, though not to the same obsessive degree as say Randy Newman.

I think of this song as an autobiographical snapshot of Steely Dan. Definitely more impressionistic.

Any Dan fan would know that Aja marked a big switch for Steely Dan's style. I think this song references that style switch, as well as Steely Dan's long reputation for being eccentric nonconformists.

An aging hipster looks at a wasted life.

Kinda sad but a beautiful song.

I like many of the interpretations here, particularly the Crimson Tide/Deacons links and Acornlev's ideas of 'die behind the wheel' referring to roulette.

As well as those already discussed, my interpretation of 'the day of the expanding man' was always partly to do with evolution, because it reminded me of the standard evolution picture you always see - of the 'ape' ancestor standing and expanding into a modern day man. Though this might seem somewhat contrived I always felt it fit well with the song, since he's feeling like a loser and can no longer fit into the "shape" which "is [his] shade, there where [he] used to stand." (the final evolution on the picture, in this analogy). I did always used to hear that as shame, rather than shade, but either works.

Still, it's a thought, even if it wasn't what was originally intended. I guess I always thought it was such a beautiful, poetic song that the first line couldn't possibly be literal.

I was struggling with alcoholism when this song came out and I heard someone in a deep depressive funk thinking how suicide would cure all the mental pain.

This song is about the decision to focus one’s life passions and energy to music. “It is the time of the expanding man” He was through with college and was through with rambling and gambling “ that’s all in the past” (or so he thought). He later wrote Boshivadtta which means enlightenment and compassionate in Hindu philosophy. Donald Fagen and Walter Becker studied philosophy and other subjects at Bard College.
The second verse is self explanatory “You call me a fool you say It’s a crazy scheme….This one’s for real I all ready bought the dream….foolish to ask me why.. throw a kiss and say goodbye”…there were some naysayers, but he believed in himself “I’ll make it this time”.. “ I’m ready to cross that fine line”...There was no looking back.
The third verse or chorus is also pretty transparent. .I’ll learn to play the saxophone. Drink Scotch Whiskey all night long and die behind the wheel ( making music and living the lifestyle is great fun …Chicks, Booze, Drugs, Sex, Death…one of there mates died in a lat night auto accident) other than the death part who wouldn’t be happy. You’ve made it….They call Alabama the Crimson Tide…. But now there is the name thing , you need a good one a cool one, a hip and catchy one after all your not Bernie the accountant, or Joe the Plumber, your in show bizzz, therefore “Deacon Blues. “ A reference to the hip coolness of the “ Steely Dan” moniker from William Burroughs “Naked Lunch” novel, whose title was miss transposed from Kerouak to Ginzberg to Burroughs from “Naked Lust”
Fourth verse “back to the wall… essence of true romance…sharing love w those we love ..& my kind…libations sensations…that stagger the mind” There were also hardships but when you are doing something you love with friends and partying and having a good time as well. The experiences are mind blowing…. Is there anything better?
Fifth verse, “I crawl like a viper…thru these suburban streets..make love to these women.. wake up when the sun goes down.. cover every game in town.(so much for focusing, partying and no gambling) a world of my own..” They moved from New York to LA, now successful players in the world stage ahh Music show Bizzz and all its fringe benefits.
The last verse he is getting ready to perform on stage again…last drag from cigarette....I cried when I wrote this song ….sue me if I play too long…..” Unlike studio sessions performing live is a high in itself and inspired players improvise and jam.. “This brother is free I’ll bee what I want to be…..” Chorus.

While I think these are all good interpretations, I think that this song is more about the songwriters expressing a mood they were in. I think it is a melancholy view of their lives up to that point. They have constantly tried to find a new "home" but are always discouraged by their experiences. If any interpretation of the song should be made I think it should be that it's about a rambler's futile search for a "home".

I put home in quotations for a reason: to draw emphasis on the connotations of the word rather then the denotations.

This song to me is a story of a guy, who is leaving his day job to become a jazz musician and the world sees him as a loser and he knows it but has reached the point where he's got to be his own man so, if you have to call him a loser then call him, Deacon Blues, since the winning Alabama football team has the pompous name of The Crimson Tide, then call me Deacon Blues, M/F! SO he's leaving being inside the corporate glass building, all that's left is his shadow there, where he used to stand....and now he's on the outside lookin in, his time is now the night, when he works in the clubs, Libations, sensations, so he turns his back to the corporate world and yeah they may be laughing at him, the loser, but Jazz bug has bitten him and he kisses the old job goodbye and you might call him a fool or crazy, but he's already made up his mind to do what his true romance is, true love, jazz. So now he plays most of the venues in Town, women, booze, music and he'll probably die behind the wheel dwi, but that's the way its got to be....etc. Yeah man! love singing this song at karaoke....

I'll put in my two cents. 1st verse tells how our character never considered himself a loser as he looked out on the 'ramblers and gamblers,' but he finds something romantic about the concept and decides he wants to be a blues man. He thinks there's nothing more to it than picking up the sax and putting feeling into it, drinking too much, and dying early as a loser with a name. He wants to have a good, exciting time, talk with the others like him, get with all the ladies, and play at night.

I think the song is much more sarcastic than many have given it credit for. The narrator isn't supposed to be someone freeing himself from society; he is naive. The idea of someone reinventing their life as a musician, not for the idea of playing music but for living hard and dying a loser, is more than a little ridiculous and should not be desirable.

Interesting notes on the football references. Very cool songwriting.