It's a Big Daddy Thing (Cold Chillin', 1989) by Big Daddy Kane

This is a phenomenal Hip-Hop album that certified Kane's status as one of the greatest.  His flow is absolutely incredible and the playboy persona that he brought to "Smooth Operator" and "Pimpin' Ain't Easy" made for great charisma.  I also give Jay-Z a lot of props for rhyming over the "Young, Gifted, and Black" beat on The S. Carter Collection mixtape and keeping his relevance known to younger audiences.  Big Daddy Kane is one of the best rappers ever and this is one of the reasons why. 

What Am I Doing in New Jersey? (Atlantic, 1989) by George Carlin

This 5-track LP covers a lot of ground.  However, there are two routines that really stand out to me.  The first is the lengthy last cut that discusses various aspects of driving.  Topics include bumper stickers, people who don't use blinkers properly, cyclists on the road, and license plates.  It's long, but packs a lot of laughs so it's totally worth it.  The other cut, which really stands out, is about politics.  But George took it in another direction and instead of focusing on actual politicians, he discusses the strange culture that policies and procedures have created in American life.  My favorite George Carlin quote ever appears here when he says, "America was founded by slave owners who wanted to be free."

Unfinished Business (Sleeping Bag, 1989) by EPMD

EPMD weren't as loud as N.W.A or as poetic as Rakim.  However, they were more relaxed like the latter.  This not only served as an excellent compliment to Erick Sermon's masterful production, but also forced the duo to deliver lyrically.  Not that they didn't before, but it was nothing that hadn't already been heard.  Fortunately, Erick and Parrish overcame the sophomore jinx and offered up "You Had Too Much to Drink"-a song speaking out against drunk driving and "Please Listen to My Demo"-one of the best records by rappers about wanting to be rappers ever.

Paul's Boutique (Capitol, 1989) by Beastie Boys

I place this album among the best-produced in hip-hop history.  Its 300+ samples will never be able to be duplicated, and its unique artistic approach merits multiple repeat listens.  It was definitely a sign of growth from Licensed to Ill, proving that Beastie Boys aspired to be more than just the mischievous punk rock/rapper guys from "(You Gotta) Fight For Your Right (To Party!)"  From beginning to end, this album is a masterpiece.  R.I.P. MCA.