This is the 23rd post in a daily series. Read about it here and see the list of previous posts here. A new post about “Star Wars” will be posted every day for 40 days leading up to the franchise’s 40th birthday on May 25th.

Jason Brannon and Chris Crawford began making comedic hip-hop songs in the late ’90s when attending Indiana University. They uploaded their songs to MP3.com under the name Bentframe, and developed a fan base. As Crawford said in an interview with Rebelscum.com:

At first we were excited because we got 50 downloads a day, then it was 200 downloads a day. That kept growing virally and we ended up being in the top 10 artists monthly for a few years, out of 300,000 artists, and we would get 15,000-20,000 downloads a day! We had a few million songs downloaded on mp3.com alone and millions more on Napster, Mozilla and other files sharing programs.

One of the songs they created was “Star Wars Gangsta Rap,” which featured raps from Luke Skywalker and Yoda, and in the verse below, Darth Vader and Emperor Palpatine:

It’s not the east or the west side.
No it’s not!
It’s not the north or the south side.
No it’s not!
It’s the Dark side.
You are correct!
Keep frontin’ the Empire,
To all you Vader-haters out there,
We’ll blow your planet up!

In the summer of 2000, Thomas Lee was a visual arts major at York University in Toronto. It was there that he first learned of Bentframe. Lee explained:

I was so impressed with just how hilariously awesome it sounded that I wanted to have a crack at animating it as a music video. It was a big deal for me as a freshman in fine arts because I was pretty much just beginning to explore the different mediums to test my artistic skills. Back then, I had never even animated before, let alone made a music video.

Lee sent the video to Brannon, who said he was “blown away.”

“Star Wars Gangsta Rap” was uploaded to newgrounds.com, where it became a hit and went viral. Time named it the best online comedy of 2001, and the following year, it won the Audience Choice Award at The Star Wars Fan Film Awards.

In 2004, an “Special Edition” version of “Star Wars Gangsta Rap” was made, touching up some of the animation from the original.

A sequel, called “Star Wars Gangsta Rap: Chronicles,” premiered in 2009.

The song — and the video — showed how much Crawford, Brannon, and Lee had grown since the original “Star Wars Gangsta Rap.” By that time, Lee was working as a professional animator, having animated a 2006 video for Weird Al Yankovic’s 2006 album, “Straight Outta Lynwood.” Lyrically, “Star Wars Gangsta Rap: Chronicles” referenced many classic hip-hop songs, like “The Humpty Dance” by Digital Underground…

Yeah, you know I’m crazy
And my skin is pale and pasty
Cuz i’m evil, I like it when the planets go boom
I once got busy in the Death Star bathroom

…and “It Takes Two” by Rob Base & DJ E-Z Rock…

I’m not intergalactically known
But I wear a blue cape at home

…and “Bring The Noise” by Public Enemy…

Public Enemy Obi-One
Stormtroopers said freeze but they got none
Can I make them say I never had a laser gun
But it’s the Jedi tricks I’m playing on your mind son

…and “I Wish” by Skee-Lo…

I wish I was 3 foot taller
I wish I was a baller
I wish I had a soft shell turtle I would call her
I wish I had a snake in a hat not a Womprat with a Tydirium Impala

…and many other songs.

“Star Wars Gangsta Rap: Chronicles” was the official follow-up to the first video, but over the years, fans had made at least one sequel. “Star Wars Gangsta Rap 2” followed a similar style as the original, though the animation was as crude as the foul lyrics.

There are some funny lines “Star Wars Gangsta Rap 2,” but it felt a little crass and lewd compared to the other versions. The rhymes in “”Star Wars Gangsta Rap” and “Chronicles” were not earth shattering, but they were at least clever.

When “Chronicles” came out in 2009, Lee, Brannon, and Crawford voiced a willingness to collaborate again, but it seemed unlikely that it would be set in a galaxy far, far away. Lee said:

Gangsta Rap, as I’ve come to find, is a great medium for comedy. I certainly wouldn’t mind working with Jason and Chris again on another song in the future. But hopefully it won’t be Star Wars themed again, because at this point, I believe we’ve finally milked it to death…

…I think it’s unlikely we’ll do anything Star Wars any time soon. But we’ll see.

That phrasing leaves the possibility open. After all, when the last video was made, we didn’t think we’d get another “Star Wars” movie either, and now we’re getting a bunch of them. So, we’ll see.

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