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As of today I have 16,448 items in iTunes. Not all of them are individual songs -- there's some audiobooks, podcasts, and miscellany, but figure there are a good solid 15,000 songs. I have 53 rated with 5 stars, the highest rating. Alphabetically:

10 Dollar [poj's cut price remix], by M.I.A.: even more insane deep bass sound than the original
All Mine, by Portishead: more deep bass, topped off by a dead-on Shirley Bassey impersonation
Ambitious, by Wire: best song about DNA ever
Ancondia, by 808 State: like Kraftwerk with a DJ
Bring The Noise, by Public Enemy: has anything this heavy ever swung so hard?
Cars, by Gary Numan: more like a 4.5, but rounded up for old times' sake
Charly [Trip Into Drum And Bass Version], by The Prodigy: cartoonish sound effects and crazy beats
Christiansands, by Tricky: great effects on the vocals, and a hypnotic rhythm track
Closedown, by The Cure: the culmination of Bob's extensive catalog of despair
Connection, by Elastica: they took Three Girl Rhumba and put in the crucial rockunroll chord change that Wire was to artsy to stoop to
Day Tripper, by The Beatles: frequently covered (my favorite is Daniel Ash's version), but the original can't be beat
Don't Believe The Hype, by Public Enemy: not as manic as some of their other singles, but another great rap by Chuck D.
Donkey Doctor, by 808 State: as energetic as the Prodigy, with great spacey sound effects
Down In It, by Nine Inch Nails: man, I thought all his stuff was gonna sound like this first single -- oh well
Euro Child, by Massive Attack: extra points for the Specials quote
Even Better Than The Real Thing, by U2: a rare groove for these guys, capped off by the "take me higher!" variation before the last chorus
Everything's Gone Green, by New Order: man meets machine
Five Man Army, by Massive Attack: unbelievably cool groove
Girlfriend, by Matthew Sweet: Robert Quine's guitar burns through this song
Hyperspeed [G-Force Part 2], by The Prodigy: "moving about 9 times the speed of sound"
I'm Only Sleeping, by The Beatles: truly psychedelic
I Am Stretched On Your Grave, by Sinead O'Connor: an Irish funeral song over James Brown's "Funky Drummer"
I Know You Got Soul, by Eric B. and Rakim: more James Brown, with Rakim's classic "pump up the volume" rap
It Could Be Sweet, by Portishead: straddling the line between cheesy pseudo-soul and pulsing trip hop
Let Me See Your I.D., by Artists United Against Apartheid: I should write a full entry about this track, and just might yet
Looking From A Hilltop (Megamix), by Section 25: the original is classic enough, but this is stripped down to a Kraftwerkian electro-groove by noted funky guy Bernard Sumner
Los Angeles, by X: John & Exene were never better together than on this tale of alienation
Magic's Wand, by Whodini: a history lesson from the days when it looked like rap might go all electro, right before Run-D.M.C. reduced it to just beats
Marquee Moon, by Television: the epic centerpiece of their classic debut album
Night of the Living Baseheads, by Public Enemy: a crazy collage of sounds and samples at a breakneck pace -- they even sample themselves!
Obstacle 1, by Interpol: Television meets Joy Division
Obstacle 2, by Interpol: spot the influences, back through Echo & the Bunnymen all the way to the Doors
One Tree Hill, by U2: not sure what this has to do with a motorcycle accident or Victor Jara, but it's truly moving, simultaneously elegiac and anthemic
Over, by Portishead: simplicity, repetition, tension
Paid in Full, by Eric B. & Rakim: self-actualization over, as Eric B. says, a "def beat"
Paperback Writer, by the Beatles: killer riff and harmonies, and the first song they did with the big bass sound
Rain, by the Beatles: the b-side to Paperback Writer, famous for its backward final verse
Rebel Without A Pause, by Public Enemy: when Chuck D. shouts "Terminator X!" and that tea-kettle whistle goes off over the James Brown shuffle beat, holy crap!
Scorpio, by Grandmaster Flash and the Furious Five: fat synth, a cheesy sequencer and a vocoder, vintage 1982
Serotonin, by Nine Horses: Peter Murphy has spent 20 years trying to make a record that sounds like this
She's Lost Control, by Joy Division: they recorded 3 great versions of this, all built around the signature bass line, but all vastly different; the album version has the insanely robotic rhythm
She Bangs The Drums, by the Stone Roses: the way this song shifts into ever-higher gears as it moves through the standard verse-chorus structure is unbeatable
She Said, She Said, by the Beatles: I don't think they ever played better on any single track
Something I Can Never Have, by Nine Inch Nails: Moby has been trying to copy this for 15 years -- the percussive effects that crash in on the chorus are genius
Soon, by My Bloody Valentine: ethereal, driving, psychedelic, swirling, epic; each element and instrument of this track are mesmerizing; the way they are mixed together is the icing on the cake
Sour Times, by Portishead: this just moves along to its own momentum
Spooning Good Singing Gum, by the Cocteau Twins: atmospheric, sure, but also catchy
Sucker M.C.'s (Krush-Groove 1), by Run-D.M.C.: I remember when I first heard this in about 1982; it was a whole different thing, and it still kicks hard today
Taste of Cindy, by the Jesus and Mary Chain: starts with one of the great opening moments in rock, then the feedback kicks in
Taste The Floor, by the Jesus and Mary Chain: like eating electric cotton candy
The Living End, by the Jesus and Mary Chain: OK, so Psychocandy is pretty great all around
There Is No Love Between Us Anymore (Remix), by Pop Will Eat Itself: a big sharp guitar riff, languid single line chorus, and crazy samples and effects in the breakdown make this an overlooked classic
Zoo Station, by U2: the distorted guitar and drums knock your head back, but the rest of this is Kraftwerk on guitar, bass and drums