For more discussion of the song selection, you may want to read our previous coverage of "Pictures of You" and of "Downtown Train," particularly regarding cover versions of the latter.
Please direct all complaints about either of these song selections to the comments below. Direct your pointless displeasure at the fact that these defeated their first-round opponents to dev/null.
As to these two songs in front of us, which is what this is about, after all, both are songs of romantic longing: in the case of "Pictures of You," it's a song of love lost; with "Downtown Train" it's a song of impossibility and desire. Both are first-person, apparently autobiographical songs, with the more obvious claim on autobiography/confessionalism going to The Cure. Though The Cure have their share of songs that border or press on into creepy ("Lullaby," anyone? that video still freaks me the fuck out), if what you prefer is the kind of unhinged homeless dude quality of desire for what he can't have, then Downtown Train's your jam. Both are romantic, though The Cure's bigger in that department than Waits. Both feature highly distinct vocals. Each video has the singer hugging themselves ("Pictures of You" at 2:04 and "Downtown Train" around the 0:30 mark). Both videos also make good use of inclement weather (at least plenty of steam in Waits), and are to say the least pretty idiosyncratic. Waits is the more unhinged of the two. If you prefer the luxuries of color, you may want "Pictures of You." "Downtown Train" features actors who aren't band members (and includes more women). It's also the more stylized of the two by a mile. Do you prefer the filmic gestures of Waits or the sort of unimaginative video of The Cure?
We think "Downtown Train" tries to play down its obvious beauty, and delivers more in terms of lyrical wit. The Cure make no such attempt toward either wit or camouflage. I think it's fair to say the production on "Pictures of You" is the better of the two by a mile. Hard to measure which of the two vocal performances conveys more distress: both singers are distinctive and unforgettable.
We're going with The Cure by 20 on this one, since we think they have the hotter hand going into today's game.
(1) The Cure, "Pictures of You"
(8) Tom Waits, "Downtown Train"