2009 was a curious time in rap. For the most part, the genre was hitting the reset button. A new paradigm of rappers emerged, soon to be major stars—Nicki Minaj, Drake, J. Cole, and Wale all made their marks. Among them was Kid Cudi with his A Kid Named Cudi mixtape and his Billboard hit/anthem for kids smoking clips everywhere, "Day 'n' Nite." Everyone in the new breed had a uniqueness and a built-in diversity, yet Cudi was still an outlier. He didn't really rap like that, but he wasn't really a singer either. It was a new kind of rap where he morphed the swagger of a rapper, the catchy hooks of a pop star, and an indie rock aesthetic.

In 2009, Cudi told Black Book Magazine, "All the hooks are stadium-worthy, crowd sing-along, powerful joints that I can't wait for people to hear in stadium magnitude. My album definitely needs to be heard loudly, but it's also a great album if you're smoking and you need to go to sleep." Reading that now it sounds like a vintage Kanye quote from the Graduation era, but that's what Cudi was—a wild man's Kanye.

The album is set in Cudi's dreams. "Everything here turns out dope," he says on "In My Dreams [Cudder Anthem]." But Cudi's lyrics brought a dark honesty that often only rappers like Scarface could muster. "When my soul was happy on my Ramen diet/Followed by a loosey was the meal of grinders," he says on "My World." Later on the same song he offers, "Niggas thought I was crazy/My mama know I stay high." It could have easily turned into a "slit-your-wrists album"—which, according to Cudi himself, it originally was meant to be, before more energetic songs were added—but the Cleveland rapper proved surprisingly adept at creating happy sounding anthems (even if, the irony was, that the lyrics were totally sad). Tracks like "Cudi Zone," "Enter Galactic," and "Up Up Away" all had an beat tempo that gave them a dreamy haze. But there was an underlying sadness and longing to it all. Much like dreams themselves, the album went every which way. —Insanul Ahmed