As great as it is, Lollapalooza can also be an exercise in exasperation. With eight stages spaced out over the huge expanse of Grant Park, it's pretty impossible to see all the acts you want to see, especially if they're playing at the same time. You're bound to face some tough decisions during the weekend, and it's too much to ask your sun- and beer-addled mind to choose wisely. That's why we're here to tackle some of Lollapalooza 2009's biggest schedule conundrums for you:
3-4 p.m. Bon Iver (Playstation) vs. Heartless Bastards (VitaminWater) Advantage: Heartless Bastards Don't get us wrong - we love Bon Iver's soft, somber (sometimes autotuned) folk. But we just heard it last year at Pitchfork, and found out that all it takes is a few annoying people next to you to drown out his strummed songs. Let's be honest, there are gonna be more than a few annoying people next to you at Lollapalooza, especially at one of the bigger stages. Better to go with something that demands your attention - the Heartless Bastards' bluesy rock certainly does that. The band's latest, The Mountain includes an even stronger sound with the addition of violin and banjo on some tracks, but really, all we need is Erika Wennerstrom's voice and we're happy.
5-6 p.m. Fleet Foxes (Playstation) vs. Asher Roth (Citi) vs. Crystal Castles (VitaminWater) Advantage: Fleet Foxes Speaking of annoying people...Asher "I Love College" Roth is sure to draw a huge crowd for his admittedly entertaining, funny raps, but do you really want to be a part of that scene? We had a tougher time eliminating Toronto electronic duo Crystal Castles from the equation, as their live shows are knows for their barely controlled chaos. But the pop-infused folk of Fleet Foxes is some of the best stuff we've heard recently: equal parts catchy and heartfelt.
6-7 p.m. The Decemberists (Budweiser) vs. Thievery Corporation (South) Advantage: Thievery Corporation It's true - The Decemberists' highly literate, often interactive storytelling makes for a great concert experience (especially if you like pirates, whales and ancient Irish and Japanese legends). But it also requires a fair amount of mental stamina, as you try to keep multiple characters (most voiced by frontman Colin Meloy) straight and remember when it's your turn to yell. Thievery Corporation asks for nothing but an open mind, as the DJ duo (and its seemingly endless stream of special guests) will take you on a musical trip featuring everything from dub and reggae to bossa nova and hip-hop. In someone else's hands, it could be an unfocused spectacle - with Thievery, it's the best party you've ever been to.
8-10 p.m. Kings of Leon (Budweiser) vs. Depeche Mode (South) Advantage: Depeche Mode Either way you go here, the UK wins. See, the Kings of Leon have enjoyed a huge following in Britain (and Europe in general) since back in 2003; Americans took a bit longer to come around to the Tennessee act, finally succumbing to the sirens of Southern rock by the time the huge single "Sex on Fire" hit the scene last year. Meanwhile, the English-born Depeche Mode has conquered the world a few times over since its electronic-pop debut in 1981, and continues to wow crowds with both its music and stage presence - the latter of which it seems the Kings haven't totally figured out yet. If we're going to admit the Brits know their tunes, we at least want to make sure we're entertained - and since this is Depeche Mode's first-ever stadium tour, you know they're gonna come with something huge.
5:30-6:30 p.m. Santigold (Playstation) vs. Glasvegas (VitaminWater) Advantage: Santigold Glasvegas' Scottish alternative rock is great and all, but does it inspire impromptu festival dance parties? Santigold does.
6:30-7:30 p.m. TV on the Radio (Budweiser) vs. Lykke Li (Citi) vs. Rise Against (South) Advantage: TV on the Radio We're all about supporting local acts, but we're also all about ingesting a hearty dose of festival fare (read: meat and booze) at Lollapalooza, and the straight-edge, PETA-supporting, vegetarian punk rockers of Rise Against will just make us feel guilty. And while Lykke Li's enchanting Swedish pop has worked its way under our skin of late ("Little Bit" is seriously addicting), TV on the Radio has long been a crowd pleaser with its mix of genres (rock, jazz, electronic) and ballsy-but-still-listenable experimentation.
7:30-8:30 p.m. Ben Harper and Relentless7 (Playstation) vs. Diplo (Perry's) vs. Animal Collective (VitaminWater) Advantage: Ben Harper and Relentless7 Speaking of experimentation, Animal Collective drew plenty of raves earlier this year for its Merriweather Post Pavilion. The group may be the future of music, but we just can't see any but the most hardcore fans getting into its brand of noise in this atmosphere. Ben Harper, on the other hand, should make a lot of people happy with his renewed commitment to rocking out (thanks to his Austin-based collaborators, Relentless7). Once upon a time, Harper put on one of the best live shows we've ever witnessed. If there's a chance he can pull it off again, it's worth missing Diplo's never-ending bag of international beats.
8:30-10 p.m. Yeah Yeah Yeahs (Budweiser) vs. Tool (South) Advantage: Tool Not to take anything away from Karen O and co., but this was a much tougher call when the Beastie Boys were on the schedule. Sure, the Yeah Yeah Yeahs offer high-energy, bounce-around-all-night rock, but Tool -- the metal band for non-metal lovers -- has long been known to put on one of the more mind-blowing shows in the business (just ask one of the thousands of obsessed fans who will be camped out by the South stage from the early afternoon on).
4:30-5:30 p.m. Neko Case (Budweiser) vs. Vampire Weekend (South) Advantage: Neko Case We don't hate Vampire Weekend nearly as much as some others. It's not (totally) the boys' fault that their debut album was hyped ad nauseum - it's still got some pretty catchy tunes. But until we hear something new from the boys (or any reports that they can actually bring some energy in a live setting), we're sticking with the Chicago-bred chanteuse whose voice knows few bounds.
5:30-6:30 p.m. Dan Auerbach (Playstation) vs. Cold War Kids (VitaminWater) Advantage: Dan Auerbach Lollapalooza loves the Cold War Kids (this will be the indie rockers' third appearance in the last four years), but Auerbach, the singer/guitarist of The Black Keys, just might become the fest's new mistress thanks to his blistering blues-rock. We've heard nothing but rave reviews about his live shows, including the one he played at Metro back in March:
6:30-7:30 p.m. Lou Reed (Budweiser) vs. Snoop Dogg (South) Advantage: Lou Reed Sorry, Snoop...this is what you get for becoming a parody of yourself. Just kidding (sort of), we would've picked against you in pretty much any circumstance. You're up against Lou effing Reed, after all. The man behind "Walk on the Wild Side," "Perfect Day," "Satellite of Love," and, oh yeah, a little band called The Velvet Underground. He may have lost a step or two over the years, but this show should still be a reminder of his greatness. Even better if he brings a tai chi dancer along.
8:30-10 p.m. Jane's Addiction (Budweiser) vs. The Killers (South) Advantage: Jane's Addiction At the risk of inflating Perry Farrell's already dangerously huge ego - you kind of have to see Jane's Addiction perform a closing set at Lollapalooza, don't you? Everything that's happened since the festival first came to Grant Park in 2005 - the over-the-top Satellite Party sets, Perry's DJ performances and Kidz stage appearances - has been leading up to this moment, and the Lolla founder wouldn't dare let us down now. Though they've rebounded slightly from their sophomore slump, The Killers are working against history here.