I've listened to "California Blue" by The Orange Peels and "Too Late" by Shoes many times separately, but I'd never heard them back to back until yesterday. That iTunes shuffle mode pairing makes sense. Both songs are about missed windows of opportunity and are lyrically sobering but musically catchy.
That's the clever trick good power pop pulls off; it leaves you feeling revitalized despite its ruminations on flawed situations. I'm curious to see if iTunes ever finds a similarly suitable segue with "Starry Eyes" by The Records.
