My mother (the psychologist) diagnosed the singer with narcissistic personality disorder based on the song 
Awww…no mention of Tears For Fears yet, and only one of Radiohead? Here I was, all psyched up to defend my favorite bands, but nooooo, can’t indulge the new guy, can you? Fine, if you won’t give me an excuse to give props to Tears For Fears, I’ll just have to do it without you.
[pretending someone mentioned TFF]
Actually, TFF was kinda pretentious back during the days of “The Hurting”. Anything after that was driven entirely by introspection, EWTRTW aside (and that was written because record producers wanted a “hit”, which is why it doesn’t sound very TFF-like), and assumes no intellectual superiority.
[/pretending someone mentioned TFF]
I’ll have to give the Radiohead mention a pass, for the most part. “Kid A” and “Amnesiac” were undeniably pretentious, even if they kicked ass (which they did) 
With “Hail to the Thief”, however, Yorke returned to writing pieces more easily recognizable as ‘songs’ in the classic sense, so I think he’s slowly but surely descending from his high horse.
oh yeah, and another one…
Candle In The Wind - “Sir” Elton John
wotta pack of smug, pretentious, insipid, treacley, overblown bull-oney.
Roland, thank you for defending Radiohead so I don’t have to do it myself. 
People, the answer is clear, though I would suspect most people here haven’t heard of the band I’m about to name. And be glad you haven’t, because everything they do takes the cake:
Godspeed You Black Emperor makes the most pretentious, intentionally-inaccessible art-rock I have ever heard. It’s barely even music. I mean, yeah, Radiohead got a little pretentious with “Kid A” and “Amnesiac”, but at least they stuck in a catchy little synth-pop parody like “Idioteque” every once and awhile.
That song IS called Bo Diddley.
Don’t know if it’s egotistical, though, because, even after hearing it a couple of times, I still don’t know what he’s singing about.
Interesting tidbit: Barry Manilow did not write “I Write the Songs.” The credit (or the blame) goes to a dude named Bruce Johnston.
I am going to go with the song Tempus Fugit by Yes, because:
A) The title is pretentious, it is latin, yet in the song they don’t ever say Tempus Fugit but instead say “Time Flies”.
B) They say “Yes” like a gazillion times.
C) The song is Yes’ typical art rock synth hyperbole.
D) The lyrics are essentially nonsense, yet have the veneer of being deep.
GovernorQuinn
Yes I was just being sarcastic - I know the song was “Bo Diddley” - and I don’t know what the heck he was singing about either.
He might be the only person to write a song about himself whose actual name is the title.
Just out of curiousity though, didn’t Barry Manilow write many of the jingles used in commercials for a stretch of the 70’s? I could be wrong on that, but if not this song could have been more true for him than anyone else.
Regarding the definition of pretentious just so I have this straight. If we were applying this to an actor, would Steven Segal be near the top of the list?
I agree that it requires taking oneself seriously. Which is why I also nominate Beautiful by Christina Aguilera. I think that was the most pretentious thing I have ever heard…and my husband makes me listen to Yes on a regular basis…
“Wedge” is British slang for money. Nothing wrong with that line.
Pretension can go in the other direction, too. Consider the output of Mr. Bruce “I’m a streetwise badass” Springsteen.
Gosh, it is so hard to be a saint in the city.
Um. No.
“Fortunate Son” by Creedence Clearwater
“I’m so much better than you cause I’m poor.”
I think the English art-rock bands of the Seventies are getting a bum rap here. Remember, “pompousness” and “pretentiousness” aren’t styles of music, they’re states of mind. You don’t become pompous when you buy a mellotron or a church organ, and you can’t avoid pretentiousness just by keeping your music simple.
That’s not to say that some of my favorite art-rock bands didn’t write some mighty silly lyrics! But Jon Anderson and Pete Sinfield at their worst never wrote lyrics as nauseatingly pompous, pretentious, phony or arrogant as Bruce Springsteen did for “Nebraska” and “The Ghost of Tom Joad.”
Those albums were very sparsely arranged- most of the songs on them featured only Bruce Springsteen and an acoustic guitar (sometimes a harmonica)… and yet, Bruce’s arrogance was as obvious as it was repellent. Every song roared “I’m not just a rock star, I’m a PROPHET, I’m a leader of my generation. Receive my wisdom!”
That kind of messianic complex makes Bruce Springsteen far more pompous than ELO or the Moody Blues could (who, really, were closer to Merseybeat than to art-rock; strip away the orchestration, and you have well-crafted, pretty pop songs) could ever have been.
Heh, I was just coming to this thread to nominate any rock song with Latin lyrics or title. That’s just willfull obscurity and bleeds pseudo-intellectualism. I can understand people calling songs with, say, French lyrics pretentious, but at least people actually speak the freakin’ language!
I’ll amend my nomination. “Stairway to Heaven” is the most prententious song that isn’t prog-rock or written by Conor Oberst.
It’s not really pretentiousness if it’s meant to be tongue-in-cheek, as I believe this one is, but I’ll mention Falco’s “Rock Me Amadeus” anyway.
“I’ll write a techno-pop song…about Mozart!” has to be worth a few points on the pretenti-o-meter. Better still, in one version of the song there’s a serious narrator who intones a list of significant dates in Mozart’s life. The final event? “1985: Austrian rock singer Falco records ‘Rock Me Amadeus’.” It takes some nerve to give yourself a shout-out in your own song, but to give that song the same weight in discussing the life of Mozart as his first concerto or The Magic Flute takes it to a whole 'nuther level.
But I do think it was meant to be funny, and it does make me grin every time. 
Bo Diddley can get away with it though, seeing as how he’s the coolest rock and roll guy ever.
Nitroglycerine
If you look at my posting #78, I thought I was saying that Bo Diddley was a cool dude. He was one of those folks who was around when it was all beginning.
[bit of a hijack]
In my folder of “strange stuff I just know I’ll want to show somebody someday,” I have a clipping from the San Jose Mercury News March 5, 1990.
The headline is, “When it was hip to be well-read”.
The byline is Stephen Holden (New York Times).
I wish I could reproduce the entire (long) article, but that’s not allowed. It is the single most pretentious, pompous, surreal piece of writing I’ve ever seen. It 's only from the headline that I’m able to surmise that the article is bemoaning the passing of a time when, at least in the author’s mind, rock and roll was bound irrevocably to obscure literary masterpieces.
This goes on for a full 30 column-inches with discussion of Bob Dylan/Dylan Thomas, Joni Mitchell/Sylvia Plath, Van Morrison/James Joyes, and (god help us) …
The big zinger is saved for the closing paragraph.
I may make that my signature.
[/bit of a hijack]