Broadcast live at Lollapalooza Festival August 5, 2007 - Grant Park, Chicago, IL, USA
The 2007 Lollapalooza set from Amy Winehouse didn’t so much unfold as it swayed and lurched its way across Grant Park in a haze of soul and heartbreak. Amy, ever the reluctant star, delivered a set that managed to feel offhand yet airtight, weaving through her now-classic tracks like “Tears Dry on Their Own,” “Back to Black,” and “Love Is a Losing Game”. Performed with the cool detachment of someone who’s lived every syllable twice. The set never drifted - every word landed, every pause mattered. She wasn’t trying to prove anything, which made it hit all the harder.
Side two of the set played like a jukebox hijack by a ska-obsessed ghost with impeccable taste. Her takes on “Hey Little Rich Girl” and “You’re Wondering Now” weren’t cute nods—they were full-bodied, brass-laced send-ups that hit with real heft. “Cupid” slinked in all woozy and charming before she dropped into the gut-punch combo of “You Know I’m No Good” and “Me & Mr. Jones,” both delivered with that perfect mix of venom and ache. “Rehab” brought the house down, of course - it had already outgrown her by then. It was “Valerie” that sealed it, Winehouse joyriding atop powered soul-pop beat like it was the most natural thing in the world. Motown via Camden Town? Piped through a cracked amp and held together with eyeliner and instinct. A set that didn’t try to be timeless, and therefore was.
Side 1 1. Addicted 2. Just Friends 3. Tears Dry On Their Own 4. He Can Only Hold Her / Doo Wop - That Thing (Lauryn Hill cover) 5. Back To Black 6. Wake Up Alone 7. Love Is A Losing Game Side 2 1. Hey Little Rich Girl (The Specials cover) 2. You're Wondering Now (Andy & Joey cover) 3. Cupid (Sam Cooke cover) 4. You Know I'm No Good 5. Me & Mr. Jones 6. Rehab 7. Valerie (The Zutons cover)
