The Underrated Comedy That Jack Black Is (Surprisingly) Most Proud Of

Jack Black and Kyle Gass first met in the mid-1980s, when the two young men were performing with the Actors' Gang, a performance troupe from Culver City, California. They bonded over their mutual taste in music, and the pair would end up spending a lot of time together at Gass' apartment, where Gass would teach Black how to play the guitar. By 1994, they had written one (1) song together, and performed live for the first time. As the lore goes, they hadn't settled on a band name yet, and put out a few choices to the audience. Their choices were the simple Pets or Meat, the silly Balboa's Biblical Theater, or Gass' favorite, The Axe Lords Featuring Gorgazon's Mischief. Eventually, though, the pair sort of insisted the audience choose Tenacious D, a term they got from a local basketball announcer (as in: tenacious defense). 

Few remember the "Tenacious D" TV specials, but the band became famous when they released their first album in 2001. The record quickly became suburban standard issue among twentysomethings, and it provided a wide audience with recordings of "Tribute," "Wonderboy," and the memorable "F*** Her Gently." Much of Tenacious D's songs were about how they were metal gods and sexual dynamos, even though the primary instrument was acoustic guitar. 

The myth of Tenacious D was fully explored in the fictional musical biopic "Tenacious D in the Pick of Destiny" which came out in theaters in November of 2006. Gass and Black wrote the film with their director, Liam Lynch, and it climaxed with a guitar battle with Satan himself (Dave Grohl). Ronnie James Dio played himself, and it featured a litany of cameos from friends and comedians. 

It tanked at the box office, and critics weren't kind. Regardless, Black has said he's very fond of the movie, and said to People Magazine in 2023 that it may be the comedy film that's closest to his heart. 

"The Pick of Destiny" is supremely silly and kind of laidback in a stoner-comedy way. Gass and Black played KG and JB, two aspiring metal musicians who just couldn't land their big break. They became friends when they realized they had matching birthmarks on their butts. The story involves the pair seeking out the titular Pick of Destiny, a magical guitar pick that is said to be fashioned from the tooth of Satan. There is a museum heist involving JB's penis. The guest stars are plentiful, and include Tim Robbins, Amy Poehler, Ben Stiller, Paul F. Tompkins, John C. Reilly, and Amy Adams. 

As mentioned, the critics disliked "Pick of Destiny," declaring it to be jejune and shaggy; it currently only holds a 53% approval rating on Rotten Tomatoes (based on 124 reviews). It has since built up a mild cult following. Black is still excited about the movie, almost 20 years later. When asked at a red carpet event (for "The Super Mario Bros. Movie") which of his many comedy projects Black remembers most fondly, he said: 

"In a weird way, it might be 'Tenacious D in the Pick of Destiny,' because that's the only movie that I wrote. [...] So, that one is actually my real baby. Maybe it's not the best, but it is my proudest."

Tenacious D broke up in 2024 after Kyle Gass said, while they were performing on their most recent tour, "Don't miss Trump next time," bitterly joking about a recent assassination attempt. Gass later apologized on social media, feeling his comment might be seen as a public call to violence, but he was still dropped by his agent. The pair seemingly came to blows over their comments, and the tour — and the band — have suspended their activities until further notice. Black has said he'll reunite with Gass when the time feels right. 

Perhaps it will be to make a sequel to "Pick of Destiny." We can all dream.