The five-minute skydiving scene, where Maxwell Smart falls from the airplane, and is saved by Agent 99, was actually shot in real life. Led by Norman Kent, a world famous skydiving photographer, a team of professional skydivers shot the entire sequence over a total of seventy jumps during a four-week period, always jumping during sunset and sunrise, to keep continuity in the scene.
In the opening scene, there is a picture of a wanted criminal on Max's refrigerator. The name of the criminal is Mr. Big, which is the name of the first villain in the original series Get Smart (1965), and the photograph is a one of Michael Dunn, who played the role.
Agent 23 tells Max that assassinations are prohibited by Executive Order 12333. Order 12333 was in fact signed by President Ronald Reagan in 1981 and had a broader purpose to require coordination between the Federal agencies and the CIA, but did reiterate an existing policy against political assassinations.
There were plans to produce a sequel but Steve Carell passed when he read the new script. Carell himself later wrote his own script that director Peter Segal liked. But between Anne Hathaway's rising success after this film and the departure of executive Alan Horn, who was shepherding the first film before he went to Disney, Steve Carell said it was unlikely that they'd make a sequel when asked during his press rounds for The Incredible Burt Wonderstone.
In the skydiving scene, Fred Whitsitt was acting as a stunt double for Steve Carell. At every jump, Whitsitt would carry a custom-made skydiving rig hidden under his jacket. When reaching the right altitude, the jacket would open on his back and allow the parachute to be deployed.
In the scenes immediately following Max's escape from the holding cell, there is a sequence featuring all of Maxwell Smart's cars from the original TV series: The red Sunbeam Tiger was Max's usual car and was seen in the opening sequence for seasons 1 and 2. The Opel GT (driven by Bernie Kopell who played Siegfried in the series) was Max's car from Season 5 when Buick sponsored the show. In the season 3 & 4 opening when VW sponsored the show, Max was shown driving a light blue VW Karmann Ghia , like the one he stole at the end of the sequence.
In the Latin American dubbed version, Agent 86 is voiced by Mexican actor Jorge Arvizu a.k.a. "El Tata," who also played the voice of the original Maxwell Smart in the Get Smart (1965) television series. Following his style, the dubbed version includes many local puns and colloquialism.
There were several Second City alumni in this movie. Steve Carell was a member of the Chicago troupe in 1991, as was Bill Murray in 1973, Alan Arkin in 1961, and David Koechner in 1994. Nate Torrence, who plays Lloyd, was a member of the Cleveland and the Los Angeles troupes, and was also a member of the Groundlings.
Max's pseudonym when he infiltrates KAOS, "Nudnik Shpilkes", is actually two Yiddish words that have crept into the English language. "Nudnik" means an annoying person (like the word "noodge") and "Shpilkes" means impatience or agitation. An appropriate description of Max at that point, from KAOS' point of view.
In the first scene in CONTROL's board room, Max plays the intercepted audio of a conversation about decaf coffee and muffins, and he simultaneously translates it to English. The original conversation is in Persian.
There are three notable cameos in the film from people involved in the original series: Bernie Kopell (the driver Max stops in the street) played Sigfried, Leonard Stern (the pilot whose plane Max commanders) produced and wrote for the show, and James Caan (the President) was a guest star on the series, playing that episode's main villain.
Leading up to the terror plot, there is a brief scene where 'the president' is reading to school children which hauntingly mirrors the real-life events of an terrorist attack on American soil, 9/11. George W. Bush was reading to schoolchildren when the towers were struck, when he was informed he carried on reading to the children and finished - some suggest this was to keep the children calm as they may have had parents who worked in the Twin Towers.
James Caan's portrayal of the President is a thinly veiled swipe at then-president George W. Bush, who was quite unpopular, particularly in Hollywood circles. In addition to Caan's character seen reading to school children (as Bush did on-camera as the 9/11 terror attacks unfolded), he also speaks with a Texas accent, mispronounces "nuclear," and is overall generally clueless; a bit of a good ol' boy and a buffoon.
While sitting in the plane, Agent 99 tells Maxwell to look at Dalip and use "peripherals" as to not be obvious. In The 40-Year-Old Virgin (2005), the character of Jay told Steve Carell's character to look at women in the bar without being obvious by using "peripherals."