20 Years Ago, Three Movies Defined Jack Black’s Career, And They All Couldn’t Be More Different

It seems that for about as long as anyone can remember, Jack Black has been a big star in Hollywood. He first came to prominence with roles in The Cable Guy and Mars Attacks! before having his true breakout in 2000 with High Fidelity. He followed that up with leading parts in Shallow Hal and School of Rock, as well as a rare unlikable turn as Carl Denham in 2005’s King Kong. However, it was a year later, in 2006, that we were treated to a trio of films that actually define Jack Black’s career. Each is an iconic staple of the era and each shows us a different side of Black’s talents.

Even though the actor had already become a star by the time 2006 rolled around, this was the year that truly cemented him. He proved that he wasn’t going to be a flash in the pan with a few fun performances. These three movies cover several genres, from comedy to romance, and couldn’t be more different from one another, yet Jack Black is fantastic in all three. He showcased the kind of range that has allowed him to remain a major player in Hollywood two decades later.

The first film starring Jack Black released in 2006 was Nacho Libre. Directed by Jared Hess, who was fresh off helming Napoleon Dynamite, this was a big character comedy for Black. The movie followed Black as Ignacio, a Catholic friar who moonlights as a masked luchador to earn money for the orphanage he works at. It was right in Black’s wheelhouse as a comedy with some heart at the center, which he showed he could nail as the lead of School of Rock.

Nacho Libre allowed him to dive deeper into the goofy side of things and show off his physical comedy skills. Having to dress up as a wrestler and get involved in the action was different for Black, yet he has never been funnier. That’s high praise, but Nacho Libre earned it. The film became a hit that proved Jack Black was a star, grossing nearly $100 million. Although reviews were mixed, there’s no denying how absurdly funny the movie is, and how great Black was in the role. Black still wants a sequel to Nacho Libre too.

A few months after Nacho Libre, we got a movie that shone a light on another element of Jack Black’s life, which is his music career. Since 1994, Black and fellow funnyman Kyle Gass have been performing as the comedy rock band Tenacious D. They even ended up with their own HBO variety show for a few years. The band was brought to the big screen in 2006 with Tenacious D in the Pick of Destiny, which blended the musical, comedy, and fantasy genres.

Tenacious D in the Pick of Destiny told a wild story of the band’s origins and their quest to find a magical pick that belongs to Satan, which would allow them to become rock legends. This was met with lackluster reviews and had a disappointing box office, but the timeless nature of Jack Black’s charisma has allowed it to become a cult classic. On top of Black’s comedic performance, the film features a fantastic soundtrack that let the world know how talented he is in that aspect of his career.

At the tail end of 2006, Jack Black tried something totally different. He starred alongside Kate Winslet, Cameron Diaz, and Jude Law in the romantic comedy The Holiday. The Nancy Meyers film is a Christmas classic that gets rewatched annually by many people, yet it felt out of place for Black’s career. While he had tried his hand at drama in King Kong, this was different, as it was a romance and he was working with established stars in that genre. He’s not who you’d expect in this kind of film.

Nancy Meyers actually created a character specifically for Black after seeing his performance in School of Rock. Meanwhile, Black admitted that he was nervous since he was cast against type, yet was excited to work opposite Kate Winslet. The Holiday was a box office success and received solid reviews, while Black was a standout in the film. That closed out a stellar 2006 that featured three iconic movies for Jack Black fans to watch.

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