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No rapper can credit themselves with a flawless discography. There are always going to be those few records which don’t work or have a handful of questionable moments that aren’t going to land with everyone listening to a certain song. Sometimes, it comes from just having many problems mounting up at once, but Redman could only point to his chemical dependency for how Dare Iz a Darkside turned out.

Then again, there are precious few artists in the music business who have kept their noses clean throughout their history. It’s never easy managing the cycle of album and tour forever, and there comes a point where something has to come along to numb the pain at least a little bit.

While Redman has never exactly been shy about his drug use in songs, Dare Iz a Darkside was always going to be a hard record to finish. Most people get the chance to stew over a bunch of tunes once they’ve got their bearings, but once the blockbuster debut comes out, suddenly, the label is convinced the latest cash cow can make the same thing within the span of six months.

And even though the album has its fair share of highlights, it’s clear there are some flies in the ointment. Some tracks tend to go on a bit too long, and like a lot of rap albums in the 1990s, it could have benefited from being trimmed down just a little bit. It’s one thing for Redman to try to make an album more ambitious for his follow-up, but if he had shaved a handful of tracks off its runtime, we would probably be looking at a respectable second outing, if nothing else.

But his drug habit during recording was getting out of hand, which, by his own admission, wrecked his judgement going into the record, telling Complex, “I was doing a lot of drugs on Dare Iz A Darkside…I swear, I have not played Dare Iz A Darkside damn near since I did it. Seriously! I was so lost, I was so fucked up during that album.”

Still, even Redman’s fall from grace is still 90% better than most MCs around the mid-1990s. Considering he had been dodging a handful of cheap shots from alleged new gangster rapper MC Hammer, letting that kind of criticism roll off his back because of how strung out he was may have been the best move he could have played.

Unfortunately, though, Redman’s case is something that’s all too real in the hip-hop community. When riding that white-hot streak, it’s impossible not to get caught up in your own hype half the time, which usually leads to songs that either aren’t as fleshed out as they could be or should have been trashed before the beat got started.

It’s completely understandable for Redman not to revisit Dare Iz a Darkside, but it offers some insight into where his head was when putting it together. This rapper was thrown into the high life and was trying desperately to keep himself from falling apart, and on half the track listing, you can hear that uneasiness in full force.