From Wu-Tang to Sinatra

A Six Degrees playlist connecting the Clan to the Chairman of the Board

The other day, I was scrolling through the tens of thousands of songs on my iPod and began thinking about the offbeat (and sometimes label-forced) collaborations involving hip-hop artists that have occurred over the past twenty years. Snoop and Miley Cyrus? Wale and Lady Gaga? DMX and Marilyn Manson?

I then began to wonder if I could connect two completely different artists simply by linking them to others with whom they’ve collaborated. As I was brainstorming this, I found that it wasn’t as difficult as I thought — Jay-Z worked with Michael Jackson and Eminem worked with Elton John so that crosses a lot of barriers — so I decided to implement a few rules to make it a bit more challenging (and, if I could pull it off, dare I say more impressive).

Rule #1: An artist that is a featured guest in one song has to be the host of the next linked song

For example, someone like Pharrell has been a featured guest on a multitude of tracks, but finding an artist that has been featured on one of his songs and then features others on their songs makes it tougher. (An exception is made in the case of duets in which both artists are billed equally on the song and the album.) This accomplishes two things. First, it makes sense visually. If you think of all of the artists linked together, it stands to reason that if you’re featured on one song, it’s just natural to then feature someone else on your song next, and so on as you go down the row. Otherwise, it’s one artist featuring a bunch of others, so that creates a hub-and-spoke effect rather than an unbroken chain.

Rule #2: The performance has to exist in either audio or video form

There are photos of Nas and The Notorious B.I.G. sitting in the studio together. There is footage of Michael Jackson and Frank Sinatra meeting during a recording session. By all accounts, Cher is on the mysterious Wu-Tang album Once Upon a Time in Shaolin, but nothing has (yet) ever come of these, so they’re disqualified. If I couldn’t find the entire song or performance, I didn’t use it at all.

Rule #3: The beginning and ending artists have to be connected in six steps

It’s called six degrees of separation, after all, so I had to be able to link the beginning artist with the ending artist in six steps.

Those are the rules, so the next question is what artists to choose?

Naturally I started with Wu-Tang Clan. Then I began to wonder what modern recording artist is as far away from Wu-Tang as possible, but could still realistically be connected to them? I considered Prince and Springsteen and Madonna, but then I realized there was really only one answer: Frank Sinatra. He was the epitome of cool throughout much of the 20th Century, he (allegedly) had connections to organized crime, and he basically lived by his own rules. In short, men wanted to be him and women wanted to be with him. Really, there was no other choice. Plus, it would be a difficult task — Sinatra not only died in 1998, but also was about as far removed from hip-hop as a modern musical artist could be.

But I was able to do it.

Here now are the six degrees of separation between the Wu-Tang Clan and Frank Sinatra:


Wu-Tang Clan featuring Nas — “Let My N — — s Live”

(The W, 2000)

Step 1

Nas featuring Pharrell — “Nas’ Angels…The Flyest”

(Charlie’s Angels Full Throttle OST, 2003)

Step 2

Pharrell featuring Pusha T — “Stay with Me”

(In My Mind, 2006)

Step 3

Pusha T featuring Kendrick Lamar — “Nosestalgia”

(My Name is My Name, 2013)

Step 4

Kendrick Lamar featuring Lady Gaga — “Bitch, Don’t Kill My Vibe” [The LG Mix]

(Unreleased, 2012)

Step 5

Lady Gaga & Tony Bennett — “I Can’t Give You Anything But Love”

(Cheek to Cheek, 2014)

Step 6

Tony Bennett & Frank Sinatra — “My Kind of Town” [Live]

(Sinatra and Friends TV special, 1977)


There you have it. From Shaolin to Hoboken in six stops.

Christopher Pierznik is the author of seven books, all of which can be purchased inPaperback and Kindle. He has written for a variety of other sites and works in finance. You can like his Facebook page here and follow him on Twitter here.

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