[3][4] The film underwent a prolonged period of development and was born out of two different completed scripts Reubens had mentioned as early as 2004: a black comedy called The Pee-wee Herman Story, where Herman becomes a singing star and moves to Hollywood; and a screen adaptation of his television series Pee-wee's Playhouse.
Pee-wee's Big Holiday began filming on March 16, 2015, and Reubens stated that the project had been greatly delayed due to script leaks.
It turns out that the three women, Pepper, Freckles, and Bella (who coincidentally goes by the nickname "Pee-Wee"), are outlaws who have just robbed a bank.
During the wedding ceremony, Pee-wee uses the disguise kit to flee the church, leaving his bride standing at the altar.
After wandering lost for a time, he comes upon an Amish community, where he entertains the locals by slowly letting the air out of a balloon, causing it to squeak loudly and shrilly.
That night when the women attempt to steal a horse and buggy, Pee-wee persuades them to leave some of their money behind for the Amish citizens to purchase a replacement.
During the rescue, the entire town of Fairville, Pepper, Freckles, and Bella (while in their prison cell), travelling salesman Gordon, the staff of the snake farm, the hairdressers, Penny King, and Grizzly Bear Daniels (who have found each other and are relaxing in Grizzly's hot tub) are watching the news broadcast (except for Farmer Brown and his daughters and the Amish people), that went national when Joe got involved.
Pee-wee returns to his job at Dan's Diner, where he shows the Fairville residents some of the items he acquired during his trip.
[13][14][15] In January 2009, Reubens told Gary Panter that the rejected first script of Pee-wee's Big Adventure (which they co-wrote) could be given a movie deal very soon, and that it would be "90 minutes of incredible beauty".
[18] In an October 2014 interview with Rolling Stone, Reubens gave an update on the status of the film, claiming its release was imminent.
[6] Digital de-aging technology was used in the film to give Pee-wee a more youthful appearance, as Reubens felt the character "doesn't work, to me, with age mixed into it."
The site's critical consensus reads, "The simple story is a little short on laughs, but there's plenty of sweet wackiness for Pee-wee Herman fans to enjoy.
"[2] On Metacritic, the film holds a score of 63 out of 100, based on 19 critics, indicating "generally favorable reviews".
[30] Upon its release, various entertainment and culture columnists made particular note of what they perceived as the film's deliberate romantic subtext regarding the relationship depicted between the story's two leads.
Slate Outward columnist Paul H. Johnson described the dynamic between the two main characters as "sweetly flirtatious", adding that, "While Pee-wee might seem childlike and sexless, his affection for Manganiello can only be called a crush.
[...] Big Holiday is a reminder that you don't have to meet heterocentric expectations: you can ride off on a motorcycle with your arms around Joe Manganiello.
And in Big Holiday, the character does something arguably even greater than come out of the closet: He resolves these identity conflicts to find happiness on his own terms.