Matthew McConaughey Hadn’t Seen The Hilarious ‘Tiptoes’ Trailer Until Tom Segura Showed it to Him

McConaughey hadn’t thought about his infamous 2003 flop for many years before going on ‘2 Bears, 1 Cave’
Matthew McConaughey Hadn’t Seen The Hilarious ‘Tiptoes’ Trailer Until Tom Segura Showed it to Him

If we were to rank the most unintentionally hilarious movies of Matthew McConaughey’s career, Tiptoes would have to be at the top of the short list.

It’s funny to think that, to Generation Z, Matthew McConaughey is just a handsome, charming, Texan prestige actor best suited for mega-budget blockbusters, Oscar-worthy roles and nothing else. Thanks to his universally acclaimed performances in lofty projects like Dallas Buyers Club and True Detective toward the top half of the 2010s, McConaughey’s mid-career McConaissance is still considered one of the entertainment business’ best-ever rebrands after the actor spent most of his early years in Hollywood playing different versions of the same shirtless romantic comedy lead, and his name on any marquee was a universal signifier for box office success and critical ridicule.

However, even during the peak-hunk years of McConaughey’s career, he still did his best to buck expectations, as was the case with his 2003 rom-com Tiptoes, which was a critical failure without the usual box office success. In Tiptoes, McConaughey played the only full-sized person in a family of little people who brings his pregnant fiancée home to meet his folks, and it’s exactly as ridiculous and uncomfortable as you could possibly hope.

Up until McConaughey’s recent appearance on the 2 Bears, 1 Cave podcast, he had never seen the Tiptoes trailer that lives as an infamous reminder of the film’s failure. But Tom Segura made sure to change that quick:

@seguratom

The plot of Tiptoes was perfectly summarized in this classic Cracked article, and the story behind the the failed rom-com is more nuanced than its hilariously off-tone trailer. Director and screenwriter Matthew Bright’s original vision for Tiptoes clocked in at a cool 150 minutes, and it supposedly told a much more touching story than what the premise of “One tall guy in a family full of little people” would reasonably suggest. Of course, Gary Oldman playing “the role of a lifetime” as McConaughey’s twin brother in full dwarf-face is questionable in any cut, but the original Tiptoes reportedly lost a lot of heart in its edit to 90 minutes, and all sense went out the window when it shrunk down to a 90-second teaser. 

Critically, Game of Thrones star Peter Dinklage played a supporting role in Tiptoes, and he has long defended Bright, Oldman and everyone else involved in the making of the film — besides its producers. Dinklage has described the original cut of Tiptoes as a “gorgeous” film, but, after the production company cut a full hour out of the original story, it became nothing more than a “rom-com with dwarves.”

Though the original good will of Tiptoes died on the editing room floor more than 20 years ago, at least its trailer is still a good laugh for its star.

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