Coolio’s song Gangsta’s Paradise and the Amish community might not seem like a match made in heaven, but Weird Al Yankovic paired them in spectacular fashion back in 1996. Coolio was quick to reject the new Amish Paradise, claiming that it was made without his approval.

Yankovic was horrified to learn that Coolio actually hated the parody. However, Coolio’s regrets were later revealed as he gave some sage advice to a student audience in 2011, telling them that his feud with Yankovic was “one of the dumbest things I did in my career.”

‘The Amish aren’t big MTV watchers’

Two decades into his comedy career, “Weird Al” Yankovic was on the lookout for a fresh challenge. He chose to branch out into rap and R&B with a parody of Coolio’s 1995 hit, Gangsta’s Paradise.

This song had topped the charts across Europe and the USA. Described as “complete pop greatness” by one critic, Gangsta’s Paradise combines the Stevie Wonder tune Pastime Paradise (1976) with vivid lyrics that reference religion and existentialism.

Coolio communicated with Stevie Wonder while making the song, hoping to win his approval. In fact, when Wonder complained about the song’s curse words, Coolio removed them completely and earned the star’s blessing.

A year later, Yankovic had created Amish Paradise: a parody track that poked fun at the extremely traditional lifestyle of Amish communities in the USA. An accompanying music video sees Yankovic churning butter, raising barns and chiding tourists.

In the barn-raising scene, the producers made a reinforced steel structure that would fall heavily around Yankovic. “I could’ve died,” he later said of the single-take moment. “…”I did some of my best acting I’ve done in my life. I had to pretend like I wasn’t scared out of my mind.”

His efforts paid off, as Amish Paradise reached the 53rd spot on the US Billboard Hot 100. The song gained plenty of fans, although Yankovic never learned how the Amish community themselves felt about the track. “The Amish as a rule aren’t big MTV watchers,” he later commented. “I haven’t gotten a lot of Amish feedback.”

‘Stay away from me’

However, one person who wasn’t pleased at all about Amish Paradise was Coolio himself. Yankovic sought permission before using Gangsta’s Paradise for a parody, and he was reportedly given approval by Coolio’s manager – but Coolio has always claimed he rejected Yankovic’s idea.

Coolio and Yankovic had crossed paths at least once: in January 1996, they appeared together at the American Music Awards to hand out the award for Famous Alternative Artist. Yankovic had copied Coolio’s famous upright braid hairstyle, and the pair laughed and joked together onstage.

According to Coolio, he had no idea at this point that Yankovic was still intent on parodying his famous song. When Coolio was given a preview of the song, he was not impressed. When questioned about the upcoming single while he was backstage at the 1996 Grammy Awards, he said: “I ain’t with that. No. I didn’t give it any sanction.”

“It ain’t like it was Beat It,” Coolio elaborated, referencing Yankovic’s 1984 Michael Jackson parody, Eat It. “Beat It was a party song. But I think Gangsta’s Paradise represented something more than that. And I really, honestly and truly, don’t appreciate him desecrating the song like that. I think he’s wrong for that, because his record company asked for my permission, and I said no.”

“But they did it anyway,” he said. “I couldn’t stop him. But you know, more power to him. I hope they sell a lot of records. Just stay away from me.”

‘I was extremely nervous’

When Yankovic heard this message from Coolio, he was reportedly “shocked” and he scrambled to make amends. In a fax message shared with his fans, he wrote: “Two separate people from my label told me that they had personally talked to Coolio at a party and that he told them that he was okay with the whole parody idea. Based on that information, I began recording the song.”

“Halfway into production, my record label told me that Coolio’s management had a problem with the parody, even though Coolio personally was okay with it,” he added. “My label told me not to worry, and that they would iron things out – so I proceeded with the recording and finished the album.”

The American Music Award appearance had caused Yankovic considerable stress. “When I did the American Music Awards with Coolio, I was extremely nervous about doing the hair gag, but he was an incredibly good sport about the whole thing, which further led me to believe that things were going to work out,” he wrote.”

In the same fax message, Yankovic noted that he had sent a “very sincere and humble letter of apology”.

Credit: Frederick M. Brown and Kevin Winter via Getty Images

Coolio never sued Yankovic, and he was happy to accept the royalties that the parody star offered. Yankovic later characterised the whole interaction as a “miscommunication” where there were some “crossed wires”.

But Coolio didn’t forget this feud anytime soon. In his 1997 song Throwdown 2000, he included the lyrics:

“If the shoe fit, put it on and stick
And if your a** uncash don’t let your mouth write no check
Fools be in the bars unadvanced with a switch
Uppercuts and fight kicks with Weird Al Yankovich [sic]”.

‘I’m not gonna fight Al’

Credit: Frazer Harrison and Pascal Le Segretain via Getty Images

Three years later, Coolio was being interviewed on the radio show Love Line when a caller asked about the Yankovic dispute. “That’s an old subject, basically I don’t even think about it anymore, I don’t care, ya know,” was his reply. “Much peace to Weird Al’s family.”

“There’s a parody law that says you can make a parody of anything you want. The person who owns the original can’t do anything,” was Coolio’s comment in 2005. “I let it go. I’m not gonna fight Al. I’m not gonna get into street s*** with Weird Al Yankovic.”

In 2006, after years of frosty relations, Coolio and Yankovic both attended the Consumer Electronics Show in Las Vegas. Coolio heard that Yankovic was in the XM Radio Booth and made his way to the area. “I admit I was a little nervous at the time, since I didn’t know if I should be expecting a handshake or a punch in the eye,” Yankovic reported.

Credit: alfredyankovic via Instagram

“As it turned out, Coolio couldn’t have been nicer – he just walked up to the table and started signing one of my pictures with his own name,” he recalled. “The cameras started going off like crazy. I don’t remember what we said to each other exactly, but it was all very friendly – and after a minute, he was gone. I turned to the next person in line and said, “Did that really just happen?””

“I doubt I’ll be invited to Coolio’s next birthday party, but at least I can stop wearing that bulletproof vest to the mall,” he joked.

‘It’s actually funny as s***’

Coolio’s U-turn on Weird Al Yankovic went unexplained until 2011, when the rapper confessed his feelings to a student audience at the Institute Of Production & Recording.

“[After the feud] I was like, ‘Coolio, who the f*** do you think you are?” Coolio stated. “He [parodied] Michael Jackson. Michael Jackson didn’t get mad… I was being too magnificent and too terrific about myself and that’s not what you want to do.”

“I’ve since apologized to him,” he noted. “Again, that was so stupid. … That was a stupid thing for me to do. That was one of the dumbest things I did in my career.”

Coolio also noted that Weird Al Yankovic had invited him to star in the 2006 movie Al’s Brain, but he turned it down because “the zeros wasn’t right”.

In another interview, Coolio elaborated, “I listened to [Amish Paradise] a couple of years after [the feud] and it’s actually funny as s***.”

Credit: Greg Doherty via Getty Images

In 2022, Coolio passed away from cardiac arrest, and tributes poured in for the rap legend. Among the stars to post messages on social media was Weird Al Yankovic himself.

He posted the words “RIP Coolio” to Instagram and Twitter, along with the photo of him and Coolio embracing at the Las Vegas show.

“That all got straightened out within a few years,” he reflected on their relationship in early 2023. “We hugged it out and we made up and I am glad there wasn’t any kind of bad blood or ill will; we were fine.”