66: "Woo Hah!! Got You All in Check" vs. "The Rain (Supa Dupa Fly)" (with Daren Jackson!)

Sometimes gangstas have happy, pleasant stories! They take cars full of girls to the Eastside Motel, and they don't even have to use their AK. Back up, back up, 'cause it's on, which story about being a smooth gangsta hits the spot for you, Ice Cube's "It Was a Good Day" or Warren G and Nate Dogg's "Regulate"?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Shawty! The year is 2007, and the twin juggernauts of Akon and T-Pain are running the charts! But can Akon's reedy tenor match T-Pain's autotuned bliss? Which is the better signature tune with the bad rap verse, "Smack That" by Akon or "Buy U a Drank (Shawty Snappin')" by T-Pain? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The dawn of '90s alternative rock, in the late '80s! Jael Holzman of punk band Ekko Astral joins us to argue about which abrasive college rock anthem stands up higher in hindsight, is it Sonic Youth's "Teen Age Riot" or The Pixies' "Where Is My Mind?"See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It's a new millennium and we're looking for THE NEW ROCK. And two fantastic garage rock bands have arrived to SAVE ROCK (or not). Which of the two big breakthrough singles of THE NEW ROCK is our favorite, "Last Nite" by The Strokes or "Fell in Love with a Girl" by The White Stripes? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Sometimes girls kiss girls, and they write songs about it, and we have feelings about it! Who did the better "I Kissed a Girl," Jill Sobule or Katy Perry? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We do love our country music women getting revenge on men, don't we, whether they're destroying beloved cars or actively taking lives! We invite "Don't Rock the Inbox" writer Natalie Weiner to help us answer who does female justice better, The Chicks with "Goodbye Earl" or Carrie Underwood with "Before He Cheats"? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

How much praise does one woman need??See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Two pop princesses blitzed the charts in 1999, and they would always be compared even though their paths quickly diverged. There's no chance that the iconic "Baby One More Time" by Britney Spears could be upset by Christina Aguilera's "Genie in a Bottle," could there?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It's the early '80s and shockingly some of the first big rap songs were by white new wave bands. But which is the best of the two big new wave hip-hop (?) hits, "Rapture" by Blondie or "Genius of Love" by Tom Tom Club?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It turns out they do still make Christmas hits! Two big pop divas have conquered the holiday airwaves in the past ten years with Yuletide jams, but which is the best, Ariana Grande's "Santa Tell Me" or Kelly Clarkson's "Underneath the Tree"?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.