The Five: Greatest Kanye West Comedy Crossovers

kanye comedy crossover

Comedians Rob Haze and Chris Daniels have officially entered the Kanye-verse to explore the cultural significance and artistic legacy of Mr. Kanye West in their new podcast, The Book of Ye. In every episode, they’re joined by a special guest to dive into a different chapter of the ever-expanding legend of the mad genius Yeezy.  The Book of Ye Podcast broadcasts on the Forever Dog Podcast Network (FDPN).  Get the details and listen here.  Rob and Chris put together the definite Kanye West comedy crossover moments for this week’s edition of THE FIVE.

It seems very ironic that Kanye West is now known to the internet as being the guy that doesn’t like to smile in pictures, because he refused to smile while taking selfies with privileged millionaire teenagers during one of the closest Super Bowls in recent history. Kanye actually has a great sense of humor and great taste in comedy. Whether it’s quoting the Adam Sandler classic “Happy Gilmore” in his song “Jesus Walks,” doing his best Napoleon Dynamite impression on the song “Monster”, or sampling the Jon Heder and Will Ferrell ice skating movie “Blades of Glory” for one of the most awesome moments in the song “Niggas in Paris”, Kanye has always incorporated his favorite comedies in his music. Rap has a long history of artists being huge fans of Gangster flicks, but Kanye has let it be known that he is a fan of “Family Guy”, “Coming to America”, and what he claims is the best movie of all time, “Anchorman”. He even made a cameo in “Anchorman 2”. Some of the biggest stars in comedy are fans of the Louis Vuitton Don as well. In this countdown, we will focus on the best moments when Kanye crossed over with the comedy world.

#5: Seth Rogen and James Franco’s Bound 3

The timing of this was the most impressive. Literally days after Kanye put out the iconic video for Bound 2 featuring him and then fiance Kim Kardashian, James Franco and Seth Rogen pull out all the stops to create a very similar video, essentially shot-for-shot. Their parody caught fire quickly online, SO much that when many people think of Bound 2 they think of the parody video first.

Rob: I am a huge Seth Rogen fan and “Knocked Up” is one of my favorite movies. I really hated Bound 3. I just felt like it was laughing at Kanye and not with Kanye. It made me think they were just trolling his celebrity rather than making something funny.

Chris: Somehow trying to grasp what’s happening in Bound 3 makes it easier for me to understand the Bound 2 video. For the record, I find both pretty hilarious.



#4: Dave Chappelle’s Kanye Story

Any Kanye fan (‘Dropouts’ as we call them on the podcast) hangs onto every detail of a good behind-the-scenes Kanye story. After a long hiatus from television, Dave Chappelle made an appearance on the “Tonight Show starring Jimmy Fallon” and told a story of meeting a young Kanye for the first time in the early days of “Chappelle’s Show” while going over sketches and listening to “The Black Album” the day it came out. If you are up on your Kanye timeline you know this means Kanye didn’t have an album out at the time. No one knew who Ye was yet, but Ye. Still, Chappelle tells a story of a 2003 Kanye displaying some of that arrogance we all know and love, even answering the phone saying, “I’m with Dave Chappelle watching skits no one has seen, because my life is dope and I do dope shit.”

Rob: When I opened for Chappelle in 2013 this was one of my favorite stories that he would tell. I remember telling my friends this story and them being super impressed with my behind-the-scenes knowledge. I was super pissed to see this story on The Tonight Show…now I need a new showbiz story.

Chris: This story is so great to me because a huge element of what made “Chappelle’s Show” so great was the musical performances that accompanied each episode. The show, not to mention “Dave Chappelle’s Block Party” brought comedy and music together in a brilliant way, and gave me a chance to see so many artists that are my idols, including Kanye.



#3: Aziz Ansari’s Kanye Fandom

Aziz Ansari was one of the hottest comedians in 2008, and no question Kanye was at the top of the rap game following “Graduation”. After Kanye announced that his tour was going to be called the Glow in the Dark Tour, Aziz decided to name his tour Glow in the Dark, and even modeled the promotional artwork after it, receiving the first of many Kanye co-signs. Kanye has made it into Aziz’s standup routine, and Aziz has even crossed over into Kanye’s world, appearing in The Throne’s Otis video. Aziz’s latest co-sign? Before Kanye got Lena Dunham all uncomfortable with his video for famous, Aziz and Eric Wareheim danced and rode bikes all over Italy in a makeshift video of their own.

Rob: I remember checking Kanye’s blog everyday around that time, and when he posted that Aziz (who at that time I only knew from Human Giant) used his tour poster I was super curious about his stand up. Then “Intimate Evenings” came out, and was instantly one of my favorite specials.

Chris: The Glow in the Dark Tour was the first time I got to see Kanye perform live. I remember leaving thinking that is what I’m gonna model my comedy tour after. Then Aziz did it. Now I will model my tour after Kate Bush.

#2: Bo Burnham’s Can’t Handle This

Kanye’s live shows have frequently featured a portion of the show where Kanye does what has been known as “the rant” where Kanye rants and freestyles about whatever he is thinking about and usually it is epic. During the Glow in the Dark Tour it was about positivity and Soulja Boy (what? It was 2008). What The Throne Tour’s rant was all about was his breakup with Amber Rose. The Yeezus tour was all about his frustrations with the fashion industry, race, and celebrity. Bo Burnham noticed this and decided to do his own autotune rant in his most recent Netflix special, “Make Happy”, though he replaces some of the serious issues that Kanye encounters with others that are much more low-stakes…like not being able to fit his hands inside of Pringle’s cans and overstuffed burritos.

Rob: The best thing about this is Bo uses the autotune in a way that really reminds you of Kanye. In 2013 after I saw the Yeezus tour, I decided to try to end my shows with a rant, but it was never like how Bo did it.

Chris: “Make Happy” is one of my favorite Netflix specials, largely because of this rant. The sound, the lighting, the mannerisms – everything is on point. And though he does his own humorous take on it, he wraps it all up in a sincerity that every Kanye rant is all about.


#1: Zach Galifianakis: Can’t Tell Me Nothing

Zach Galifianakis is one of the most unique and fearless characters in comedy, with a very unorthodox style. On the Comedians of Comedy Tour, Galifianakis even picked up a doo-wop group off the street and made them a part of his act. In 2007, he started making unexpected and hilarious music videos of himself lip-syncing Anita Baker songs. The story goes that Kanye attended one of Galifianakis’ shows in L.A. and loved it so much he had to have him appear in the video for “Can’t Tell Me Nothing”. Zach created a video to the song that is totally different from the original Hype Williams directed. Galifianakis’ version takes place on his farm as he lip-syncs the song while hangs out with Will Oldham, does some farm-hand labor, tends to his cows, rides his tractor, and some other goofy shit, backed by what might be Amish backup dancers. People who didn’t have a pulse on much of the alternative comedy scene might not have been witness to the hilarity of Zach Galifianakis until The Hangover, but Kanye fans were most likely introduced to him because of this video.

Rob: When I was in college I remember my roommate putting me on Zach Galifianakis and I putting him on Kanye and when this video came out it was like our worlds collided.

Chris: Simply put, this is one of the greatest music videos of all time. I just wish Maria Bamford had made a cameo.


Honorable Mentions:

There are other moments that could not crack the top five that are nothing short of amazing. The video of John Mayer and Kanye working on “Bittersweet” was hard to knock off the list. John Mayer, who has done stand up comedy sets, and even had a comedy show on VH-1 is hilarious in it. This is way before Mayer made those problematic comments in Playboy magazine and it was way easier to laugh with him.


Before the album Graduation dropped in 2007, Kanye went to London to host the Friday Night Project. This is one of the first times we see Kanye’s humor and he pretty much steals the show. It is an hour long show that includes skits, interviews, pranks, and games all centered around Yeezy.

Kanye may have had issues with SNL, but he has made some funny sketches on there. He was even a part of the SNL 40 celebration. This 2007 pre Taylor Swift sketch about his behavior at award shows is one of the funniest. It was so good, Kanye busts out a freestyle during his performance.


Rob Haze is a comedian from Atlanta, Georgia. He was featured as a New Face in the 2015 Just For Laughs Comedy Festival, won the prestigious Laughing Skull Comedy Festival in 2015, and was featured on season 9 of  Last Comic Standing. Chris Daniels hails out of the Michigan comedy scene, before moving to his current home of New York City. He has performed at the Detroit Comedy Festival, Gilda’s LaughFest, the Brooklyn Comedy Festival, and has had work featured in the pages of Valiant Comics.

Read more comedy news, stories, interviews with comedians, videos and comedy clips on our home page. Get more comedy news. Watch more viral videos. Read more interviews with the best comics in the business.


The following two tabs change content below.

Rob Haze and Chris Daniels

Latest posts by Rob Haze and Chris Daniels (see all)