2001: #2- "Ms. Jackson"

Ten times out of nine, a songsmith who chooses the heartfelt route will falter not necessarily by way of lyrical sentiment but in the arena of not-being-shitty. Who really wants to listen to a guy pouring his heart out apologizing for being misunderstood unless the beats and the rhymes are dope? With "Ms. Jackson", like a swirling pop-rap/funk combination of say, Prince and 2Pac, Outkast gets the tone totally right.

The layers of synths create drama but not melodrama, and the layers of imagery within the words evoke more than vague, simplistic angst - for the most part, we're listening in on the sincere, thoughtful, witty and painful musings of two grown men who just want to make good with their babies' mamas' mamas, using some of the more unique imagery in hip hop's history of course.

Favorite lines? We like the idea of apologizing "a trillion times", as if the quantity would help the futile situation; "I love your mom and everything, but..."; rhyming divided with invited with despite it; "puppy love" vs. "full grown" love; the house with the tire swing; the knee pads line; and of course the whole thing about the picnic.

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2003: #6 - "The Way You Move"

(Not the official video - sadly, Outkast and their people join the awful cast of characters who disable embedding of their videos)

"The Way You Move" was another out-of-leftfield move in the idiosyncratic career of Outkast. Not content with being masters of Southern-fried G-Funk, they moved on to Southern-fried, outer-space P-Funk in the late 90's, before assaulting the pop charts in the 2000's with a flurry of ferociously original but fun pop-rap hits. Big Boi's "The Way You Move" was an outlier, even in this bunch - a slow-burning Miami-bass sex-funk song, 808s building up into a groove accented by sassy horns, soulful vocals, and Big Boi's ever-evolving conversational delivery. At the end of the first verse, we're not sure if he's giving it up to a bassy speaker system or to womanly anatomy ("Trunk rattlin’, like two midgets in the back seat wrestlin’"), but either way it's a great image.

2004: #2 - "Roses"

Please ignore the corny faux-blues piano intro - "Roses" is the slightly cooler, more melodic, less gimmicky older brother of "Hey Ya!". There's nothing very unique going on structurally or sonically - though the multi-track, pitch-shifted vocals (downward, for a sci-fi P-Funk feel rather than the usual Chipmunks) are awesome - but the melodies are incredibly strong throughout the entire song, and lyrically, both Andre and Big Boi continue to push the boundaries of what we're used to hearing in pop and hip hop songs. It's tough to pick just one standout image - there are golden calculators, poo-smelling roses, and a plea for some "support, bra", among many others - so we won't. "Hey Ya!" was the song everyone talked about, "The Way You Move" was the song that we all could agree on, but "Roses" was the song that kept us coming back, and still holds up more than a half-dozen years later.

2008: #3 - "Royal Flush"

Big Boi, Raekwon and Andre 3000, together again. The last time these three teamed up - on 1999's "Skew It On the Bar-B" - we got snappy, hard, yet minimalist stuttering synth-funk, carried lyrically by such impressive, distinctively unique verses it was hard to pick a favorite. Right now, we'd go with Raekwon's, where he spends 45 seconds rhyming things with "hydro". But more on that at a later date.

Does "Royal Flush" live up to its predecessor? Of course it does; would it be #3 otherwise? Let's break down why. This time around the funk is even funkier, with a slower, harder beat and a more sinister synth-bass line that's actually as memorable as any Top 40 hook of the year. Big Boi shouts through a tight, angry verse (on President Bush: "Iraq, 'I that', now he gunnin' for Iran"), talks nuclear war and gives way to an Isley Brothers sample via Billy Ocean reference ("Billy Ocean/body floatin'/take a voyage to Atlantis"). After the "break", Raekwon is next, and he hands off almost as soon as the beat starts to build back up, as if to clear the way for Andre 3000.

Now, in the last decade, Andre has built up an image in the mainstream as a funky, silly, quirky, well-dressed, psychedelic, singing, dancing, acting, sensitive hippie rocker ladies-man - a cross between Jimi Hendrix, Elvis, Prince and George Clinton, but a very minor version, taking only the most superficial and annoying elements of each legend. Perhaps this public perception holds some weight, but it's far from the whole picture. Before he stepped into the limelight as a fashion icon/movie star, Andre was considered to be one of the very greatest lyricists in hip hop history. And in the late 90's, he was THE king. Here he sets out to reclaim that throne.

For nearly two whole minutes, he owns this song. When he comes in during the third verse, percussion elements that were in the song earlier are actually removed from the beat, perhaps to give the audience a completely empty stage with a spotlight shone directly on the man. The man comes through in the clutch with one of his top 5 verses ever. It's funny, clever, deep, full of great metaphors, references, twists and turns, and some of his trademark pauses and oddball rhyming schemes. Please listen, as descriptions do not do it justice.

2009: #2 - "Shine Blockas"

Though the members of Outkast have been going for the jugular since the late 90's - they did weird, sprawling psych-funk on the epic album Aquemini, then tried big, noisy yet intricate pop on the equally sprawling but radio-ready epic Stankonia, then threw everything they could on the really really sprawling double album Speakerboxxx/ The Love Below - they can still be counted on for the effortless, laid back Southern rap anthems they used to do so well ("Southerplayalisticadillacmuzik", "ATLiens").

Case in point: Big Boi's latest single from Sir Luscious Left Foot, his first solo album, release date TDB (Seems any label in their right mind would want to put out an album containing this one, and last year's "Royal Flush", but we digress).

It can be difficult to describe why something that's so cool without being clever, so smooth without being obvious about it, and so well-orchestrated without being busy or trying too hard is so great. So, maybe we won't. Just click on the video (which looks like it cost about $700 to make) and listen to a quintessential 00's - lush, dense, and full of pitch-shifted samples - rap masterpiece.