Coolio
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I have to admit, I rolled my eyes when I discovered that this week was the anniversary of Coolio’s sophomore album, Gangsta’s Paradise. Coolio? With the crazy braids? (Unlike most old-school trends, Coolio’s braids looked (almost) as ridiculous then as they do now). From what I could remember, Coolio was just that rapper with that one huge song in the film Dangerous Minds with Michelle Pfeiffer. Does he even deserve a Cheat Sheet? Actually, after doing my homework, I realize that he absolutely does.

Everything you need to know about: Coolio’s second album, Gangsta’s Paradise, released 20 years ago, on Nov. 21, 1995.

Pretest: Which legendary R&B singer, who is currently on tour­ performing his magnum opus in its entirety, had a single from that legendary album be heavily sampled on Coolio’s hit single? (Name not just the entertainer but also the album and the single!)*

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Extra credit: Coolio performed the theme song for which ’90s Nickelodeon show?**

Background research: The album, which sold 3 million copies, was almost universally acclaimed. Entertainment Weekly gave it a B-plus and later named it one of the top 10 albums of 1995. In 2008, VH1 named it one of hip-hop’s greatest 100 songs. And The Source, known at the time as the final word on hip-hop excellence, awarded the album four out of five mics.

Why Gangsta’s Paradise matters: Besides all of the above, the sheer impact of that lead single just can’t be denied: The song went to No. 1 in more than a dozen countries, won a Grammy for Best Rap Performance (beating out the Notorious B.I.G., Dr. Dre and Tupac!), and it was 1995’s overall No. 1 single among all genres. And the album as a whole wasn’t dependent on just that runaway single. The songs “Too Hot” and “1, 2, 3, 4 (Sumpin’ New)” showed that as a lyricist, Coolio wasn’t a powerhouse—but he was no slouch, either.  

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The essential two-song playlist: Not gonna listen to the whole album? It’s OK. The album was good. But truth be told, there were several skip-worthy tracks. And even though he dropped decent singles from the album, let’s be honest: The only song that’s truly essential on this album is “Gangsta’s Paradise.” A close second would be a track called “For My Sistas.” It’s a heartfelt love letter to women—from someone who knows his actions don’t always match his intentions. So for this week, the three-song playlist is actually just two songs.

But is this album really essential for you to know? Do you need to know the whole album? Debatable. The single? Yes, it’s a need-to-know song. Coolio doesn’t reinvent the wheel on this album, and the lyrics often have a touch of gangsta-lite posturing. But that massive first single introduced a generation of listeners to the extraordinary beauty of a flawless melody and vocal arrangement composed by one of the finest musicians in modern history. (See the pretest.) If for no reason than that one, Gangsta’s Paradise is essential.

Report card: I just streamed the entire album to give it a 2015 listen and an updated rating. (You’re welcome.) In addition to the first few singles and the aforementioned “For My Sistas,” there’s a winner in “Kinda High Kinda Drunk,” a playful ode to party nights. The album? A solid B-plus. Those braids? A D-minus.

In related news: The single “Gangsta’s Paradise” owes a great debt to little-known singer L.V. The Los Angeles native had some big shoes to fill while singing the hook. (Again, see the pretest.) While he doesn’t come close to the original, his voice was strong enough to make Coolio’s version land a heavy musical punch.

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* Pretest: This was an easy one, right? It’s Stevie Wonder! He’s currently on tour, performing his landmark album, Songs in the Key of Life, in its entirety. One of the album’s songs, “Pastime Paradise,” was heavily sampled on Coolio’s “Gangsta’s Paradise.”

** Extra credit: Coolio lent his rapping talents to the theme song for the ’90s Nickelodeon series Kenan & Kel.

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Aliya S. King, a native of East Orange, N.J., is the author of two novels and three nonfiction books, including the New York Times best-seller Keep the Faith, written with recording artist Faith Evans. She lives with her husband and two daughters in New Jersey. Find her on Twitter and at aliyasking.com