* CoveredUp: Most of the soundtrack consists of popular artists of the time performing covers of lesser-known Steely Dan songs.
* CrossesTheLineTwice: At their worst, Hank's actions are played as BlackComedy.
* HarsherInHindsight: The film makes jokes about Irene's slender frame, with Charlie's sons proclaiming that their father wouldn't run off with "a skinny-leg girl" and Hank jesting that she used to develop an eating disorder and gained about 20 lbs; with the knowledge of [[ReneeZellweger Renee Zellweger's]] own WeightWoe as a result of the 20 something pound weight gain to play BridgetJones and the [[YouAreFat press's own negative attention]] towards her [[HollywoodPudgy post 1970 Hollywood atypical curves]] and her rapid weight loss after the completion of the films, the dialogue can come off as awkward and insensitive.
* [[HeyItsThatGuy Hey, It's That Guy!]]: Shannon Whirry, 90's erotic b-movie queen, aptly plays the endowed mother.
* HilariousInHindsight: One of Charlie's sons exclaims "Man, how the hell can they call Pluto a planet - man what kind of planet has an elliptical orbit? This shit don't make sense!" Pluto was demoted in 2006, six years after the movie was released. while we're at it...
** CriticalResearchFailure: Almost all planetary orbits are at least ''a little'' elliptical. A true oddball orbit would be a perfect circle.
* ShoutOut: The narrator is voiced by Rex Allen, Jr., the son of Rex Allen, who was the narrator of many Disney wildlife films. One of which was Charlie the Lonesome Cougar. The narration was done in a way to mimic these films.
* TheWoobie: Charlie. The second you see his kids being born you will feel sorry for him, and it only increases as the film goes on and you learn that the entire town is laughing at him behind his back and he knows it, but is too nice to do anything about it.
** JerkassWoobie: Hank. He's the one who has had to deal with all of Charlie's repressed rage for twenty years or so, and never gets out to express it. He also notes to Irene that before Charlie's wife left him, their personality was more integrated; when she left, she left both of them, and that was the point when Charlie split off the Hank personality and locked it away. While obviously no excuse for his actions, it does make you feel for him, especially when he begins crying.