Trying to track down a crime comedy I watched as a child in the early 2000s

I was born in 1990 in the UK, and when I was about 11, give or take 2 years, I remember watching an American crime caper, which my mother and I rented (probably on DVD) from the local Spar. Given my age, it would likely have been released in the early 2000s, possibly in the late 1990s. I don’t remember the film as being particularly good, but it’s stuck in my memory – so much so that, over the last ten years, every few months a kind of mania comes over me for a day or so, and I obsessively try plugging various terms into Google – to no avail. Sometimes I think I must have dreamed the whole thing!

Despite the rather bleak plot points I’m going to enumerate, I remember it had a rather light, humorous tone throughout. Here’s what I remember:

1. The whole plot takes place over one night; the opening scenes take place at dusk, and the closing scenes take place at the following dawn.
2. Chronologically speaking, I think the film was fairly linear, but there were three or four (perhaps more) intersecting storylines, each centred on a particular character.
3. The character with the most screen time was a “cool guy” – in my mind’s eye, he looks like a cross between Sam Rockwell and Chris Pratt, although I’m pretty sure he wasn’t portrayed by either of them, and he wears a stylish brown leather jacket – who was trying to set up a small time drug deal, which inevitably goes wrong, although I can’t remember how exactly.
4. Another issue which this cool guy has to grapple with is rescuing his disabled mother from the care of his malevolent father.
5. The malevolent father is very much a moustache-twirling villain. (I should say that I don’t remember him having a literal moustache!) I seem to remember that he was an old man played by a much younger actor wearing bad prosthetics. I definitely remember the cool guy character, in a voice-over, describing his father as ‘basically your typical Republican’ – which, looking back, seems like a standard popular culture sentiment in the Bush era. (That might not be the exact form of words used, but it was very close to that.)
6. In a memorable scene close to the end of the film, the cool guy chases his father over rooftops in the early morning sunshine. I remember that a fire axe was involved, but I can’t remember who was wielding it.
7. The other storyline which I can remember was a rape-and-revenge tale. A character’s backstory was that she had been gang-raped, and part of the film involves her tracking down and killing her attackers.
8. In a scene which naturally seared itself into the memory of an 11 year old boy, the rape survivor confronts the ringleader of her attackers, whom she’s tied to a chair. She grabs his genitals through his clothing, and he looks at her pleadingly and shakes his head. Then the camera pans away while the audience can hear her blowing off said organs with a shotgun.
9. I can’t remember anything about the other storylines.

Other points to note:

1. It’s definitely not Go (1999) – although it is strikingly similar to that film in a number of respects.