Anderson deliberately wanted to make a very different film after the rigors of making Magnolia (1999). He felt he had reached a dead end with his previous multi-character movies and he also wanted to subvert the critics' expectations of his films.
A subplot of the film was inspired by an article in 'Time' magazine about David Phillips, a University of California civil engineer who stumbled upon a lucrative frequent-flyer promotion. By purchasing 12,150 cups of Healthy Choice pudding for just $3,000, he accumulated 1.25 million air-miles.
During the scene where Barry is at the supermarket looking for the cheapest Healthy Choice food item, he is being followed by an out-of-focus character in a red outfit. It's Emily Watson's character, before they've been introduced.
At one point in the film, Adam Sandler (Barry) is being followed by the Steadicam as he talks on the phone. During one take, the front of the camera accidentally bumped into a table and knocked the camera briefly, causing the shot to jump from Sandler to an image of an out-of-focus piece of the set and then quickly readjust. Paul Thomas Anderson loved the effect and wanted to do it again, so the crew did more takes and right at the same point in the dialogue, they smacked the front of the matte box on the camera to reproduce the effect.
During promotional interview for Magnolia (1999), a British journalist asked director Paul Thomas Anderson which actors he would like to work with in future. Anderson replied that he would like to work with Adam Sandler and Daniel Day-Lewis. The journalist believed Anderson was joking, because the two actors are from such different backgrounds and have very different acting styles. However, Anderson's next two films did indeed feature these two actors in the lead roles (this film starring Sandler, and There Will Be Blood (2007) starring Day-Lewis).
Paul Thomas Anderson first announced that his follow-up to Magnolia (1999) would be an Adam Sandler comedy at a press conference at the Cannes Film Festival. The news was greeted with laughter by the assembled press. When "Punch-Drunk Love" eventually played at Cannes, Anderson won the Best Director award and was nominated for the festivals' top prize, the "Palme d'Or". Months later, Sandler was nominated for a Golden Globe in the "...Musical or Comedy" category.
When Barry begins to tell Lance about the extortion scheme he has become a victim of, at one point Adam Sandler suddenly stares at the pudding on his desk. Just before he looks, an electronic voice on the film's sound-track faintly says, "Come here, Barry."
Unusually, Jon Brion composed music for the film while filming was taking place, experimenting with tones and sounds, making particular note of what director Paul Thomas Anderson was responding to. Brion's score would then be played on set, helping to influence the tone of the film.
For the film's publicity tour, writer/director Paul Thomas Anderson agreed to do far fewer interviews than on his previous two films. In the years since the film's release, Anderson has consistently declined to discuss either the film itself or its production.
Just as the film was entering production, the long-term relationship between star 'Mary-Lynn Rajskub' and composer Jon Brion came to end, which meant that during the scoring process there were days where Brion was forced to watch his ex-girlfriend on-screen for up to 8 hours at a time. In order to heal from the experience, Brion urged Fiona Apple to work on some songs for a new album. Coincidentally, the resulting album was "Extraordinary Machine", which is widely speculated to be about Apple's break-up from the film's writer/director, Paul Thomas Anderson.
When Barry says, "Business is very food," it was actually only a typo that the director decided to keep. In the movie Popeye (1980) there's a song called 'Everything is Food' (though not included on the sound-track album) by Harry Nilsson. The song 'He Needs Me', by Harry Nilsson, which is featured prominently in 'Punch-Drunk Love', is originally from the Popeye sound-track. This is a strange coincidence because while Barry used the word "food" in place of "good" as an accidental slip of the tongue which originated from an error in the script, in Popeye the word "food" was used in place of "good" as an intended play on words.
We can see in a scene the name of the car repair shop, the real address and phone number: Eckhart Auto Body 10101 Canoga Avenue, Chatsworth, CA 91311 (818) 882-1396 If you search it in Streetview you can see the exact place where most of the picture was filmed.
Shots of Adam Sandler running frantically from the four brothers are shot using a tracking camera. This was repeated in a later Paul Thomas Anderson movie, The Master (2012), as Freddie Quell, runs from the angry farm workers.
John C. Reilly was originally to play one of the men who come from Utah to collect the money. But Reilly thought that it was a strange role for him, considering how people would recognize him and wonder why he was not doing more. So he dropped out. Reilly would later appear in another Sandler film, Anger Management, also featuring Luis Guzman.
A fake commercial for Dean Trumbell's mattress store was shot but cut and released as a DVD extra. The scene is a remake of a real circulated video known as "The Mattress Man". A fake asphalt floor made of cushion was used for Philip Seymour Hoffman to after hopping off a set of mattresses to give the illusion of hurting himself on the ground.
Pink is a prominent color in the scenes shot in Hawaii. The lamp on the outdoor table, the hotel pillars, a painting in the hotel, the Hawaiian singers' clothing, and many other things all are pink or light magenta.
The address listed to return the frequent flyer promotional coupon is Healthy Choice Frequent Flyer Offer, P.O. Box 440201 Dept A, El Paso, TX 88544-0201. This is almost exactly the listing from the original promotion, except the second line read "Dept. A" instead of E. The ZIP code is also incorrect. El Paso ZIP codes begin with 7.
Reversing an audio recording of the name "Lena" yields "añil", a plant source for indigo dye. For most of the film, Barry is shown wearing his strikingly indigo-colored jacket. Together, her name and his color form an aural symmetry.
Paul Thomas Anderson: [iris in/out] After Barry and Lena have gotten together in Hawaii, there is a shot of them walking down a hallway, away from the camera. They hold hands, and the shot closes with an Iris Out, the circle going around their hands.