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.
During promotional interview for 'Magnolia', 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' starring Day-Lewis).
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.
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.
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 Palm d'Or.
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 onscreen 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. Ironically, 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.
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.
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.
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. Being a close friend of Adam Sandler, it seemed like a natural fit to make a project with him.
Shots of Adam Sandler running frantically from the four brothers are shot using a tracking camera. This was repeated in a later P.T. Anderson movie, The Master, as Joaquin Phoenix's character, Freddie Quell, runs from the angry farm workers.
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.
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.
For much of the movie, Barry (Adam Sandler) is obsessed with store-bought pudding cups. In 1995's Billy Madison, Billy (also played by Adam Sandler) is particularly fond of pudding cups in his school lunch, or 'Snack Pack' as he refers to them.
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.
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:
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.