In 2006, Lupe Fiasco emerged as one of the freshest voices in hip-hop with his debut album, "Lupe Fiasco's Food and Liquor."

It presented the rapper as a nerdy, skateboarding street poet who acknowledged that he had been shaped by the ghetto even as he detested how rap had exploited ghetto pathology for profit. The music defied hip-hop convention, mining Filipino jazz, Burt Bacharach and Al DiMeola for inspiration.

Fiasco, born Wasalu Muham-med Jaco 25 years ago on the West Side of Chicago, takes even more chances on his second album, "The Cool" (1st and 15th/Atlantic), out since Dec. 18. It includes a four-song mini-narrative revolving around three characters — a hustler (the Cool), a menacing father figure (the Game), and a temptress (the Streets) — that ends tragically.

In the process, Fiasco asks, "What is cool?" The question hovers over an album in which the rapper muses about the corruption of fame, the emptiness of gangsta rap, and the perils of cheeseburgers. It's a minefield of potential preachiness, and Fiasco doesn't come out unscathed. If the first album had a glide to its step, a breeziness that defied some of its introspective subject matter, the follow-up immerses itself in darkness. It's heavier in every way, and not always for the better.

When Fiasco dials down the finger-wagging, he's a master entertainer. Though "The Cool" contains a high-profile cameo from Snoop Dogg, Fiasco once again primarily works with longtime associates such as the producer Soundtrakk and the vocalists Matthew Santos and Sarah Green. Big-name producers might've brought him a few beats more in line with rap's commercial norm. But the norm has never been Fiasco's focus. Instead he fashions his own version of cool: simmering beats closer in feel to jazz than funk, breezy melodies, and dense word play that invites listeners to think while they bob their heads.

He opens up his sound even further by collaborating with Fall Out Boy's Patrick Stump on "Little Weapon," a gripping narrative about African boy-soldiers, and with British producer UNKLE and Queens of the Stone Age guitarist Josh Homme on "Hello/Goodbye," a pummeling collision with "oblivion."

Only at the tail end of the album does Fiasco embrace cliché, with a rare lusty escapade, "Go Baby." But in the context of what has come before, it's a well-earned opportunity to blow off some steam.

Make a difference. Donate to The Advertiser Christmas Fund.