De La Soul is Dead (Tommy Boy, 1991) by De La Soul

This album is incredible.  As far as skits are concerned, it's flawless.  Prince Paul is not only a fantastic producer in terms of music, but also in terms of bringing the best out of De La.  "Millie Pulled a Pistol on Santa" and "A Roller Skating Jam Named "Saturdays"" are daring and incredible singles, and lyrically the album drops pop culture references better than most.

Naughty by Nature (Tommy Boy, 1991) by Naughty By Nature

"Some get a little and some get none/Some catch a bad one and some leave the job half done/I was one who never had and always mad/Never knew my dad, motherfuck the fag/Well, anyway, I did pick ups, flipped the clip up/Too many stick-ups, 'cause niggas had the trigger hic-ups/I couldn't get a job, nappy hair was not allowed/My mother couldn't afford us all, she had to throw me out/I walked the strip, which is a clip, who wanna hit?/They got 'em quick, I had to eat, this money's good as spent/I threw in graves, I wasn't paid enough/I kept 'em long 'cause I couldn't afford a haircut/I got laughed at, I got chumped, I got dissed/I got upset, I got a Tec and a banana clip/Was down to throw the led to any tellin' crackhead/I'd still a' been broke, so a lot of good it woulda did/Or done, if not for bad luck, I would have none/Why did I have to live a life of such a bad one/Why when I was a kid and played out was a sad one/And always wanted to live like just a fat one"

-Treach, "Everything's Gonna Be Alright"

It Takes a Thief (Tommy Boy, 1994) by Coolio

Coolio's debut album is a very interesting one.  West Coast hip hop was very gangsta at the time, and Coolio's subject matter covered some of the same topics.  Yet, he spoke about these things with a sense of humor, vulnerability, and humility that a lot of hardcore rap didn't.  "County Line" discussed standing in the welfare line and "I Remember" is about getting shot by a gang member for unknowingly wearing the wrong colors.  Gangsta's Paradise is a great album too, has a great deal of sentimental value to me and was very successful.  Perhaps though, the only downside to its achievements is that it overshadowed Coolio's great piece of work from a year earlier.

Whitey Ford Sings the Blues (Tommy Boy, 1998) by Everlast

The fusion of rap and rock works a fair amount of the time, but the combination of the two very often sounds deliberate.  However, in the case of this album, it sounds very organic and that makes for a very enjoyable listen.  Not only does Everlast rap like he did with House of Pain, but he also infuses rock and a touch of folk and blues.  "Ends", "Hot to Death", and "What It's Like" are all outstanding.  Considering his heart condition and the surgery that followed while making this album, it's a very personal recording.  Without question, it is Everlast's best work to date.

Gangsta's Paradise (Tommy Boy, 1995) by Coolio

This is the album that got me interested in hip-hop.  "Gangsta's Paradise" is of course a big song, but it has a lot of sentimental value as well.  I'll never forget roller-skating parties in third-grade and the way everyone would react when that song came on.  But there are other strong points on this album as well, "Geto Highlites" is phenomenal with the Eazy-E and Magic Johnson references.  "Kinda High, Kinda Drunk" is a great party song, and "Bright As the Sun" is a solid song about the ghetto birds.  Even though he didn't say it as blatantly as N.W.A, don't get it twisted Coolio represented Compton too.  But he was able to have  fun as well, instead of just providing a soundtrack to chaos.