Jake's ex fiancé was abusive to him, which is why he left her.
Additionally, the reason she also seems to hate Elwood is, because he urged Jake to leave this toxic relationship and stay with him. Addendum: The Mystery Woman is a Mob Princess.
Her father asks a favor of "Mad Pete" Trullo? The best Romanian caterers in the state? Access to multiple and in several cases nigh-impossible to procure weapons systems? Elwood probably saved Jake from getting killed by ditching her.- At the very least, she heavily implies she has connections, so at minimum her father, if not a made man of some kind or outright mob boss, does something important for the mob, like a hit man or accountant.
- Now why does she go after Jake and Elwood instead of one or several professional hitmen? Easy: She doesn't have any connections to the mob whatsoever otherwise. And as the extended cut reveals, Burton Mercer, a plain-clothes detective, seems to know Elwood pretty well due to being the only cop in town who knows Elwood's actual address and has been there before. Mercer may come over as a Bunny-Ears Lawyer, but if someone like him catches a whiff of the mob, and be it by his current target person being killed by a hitman, the mob is done. And I wouldn't be surprised if the Mystery Woman's father has already seen one of Mercer's business cards, too.
The movie is a tall tale
told by one of the orphanage kids who helped Curtis publicize the Blues Brothers' gig, to his own kids decades later. This helps explain the crazy awesome overkill of it all. Most of the events really did happen, just more realistically. The Brothers probably stole a gig, ran from cops, came late to their own show, et cetera—but they probably didn't get chased by the police, Illinois Nazis, the Good Old Boys, and the Mystery Woman; The song "Think" was probably a spoken conversation; and so on. But it was still crazy and awesome enough for the kid to remember it fondly and add more awesomeness to it in his adult days. Curtis is God.
He first appears to the boys in a church, is a much kinder and gentler religious voice than the Penguin, gives them directions to the church where they "see the light", and magically appears in an all white tuxedo for his big solo number.- Given that God in Bruce Almighty is an old black man, this seems to fit.
Elwood didn't break his date with Twiggy.
"It's 106 miles to Chicago". Going the speed limit (assuming the standard 55 MPH), it should take about two hours. Assuming the show ended around midnight or just before, they should have been in Chicago by 2 AM, earlier since Elwood Drives Like Crazy, but they're still on the highway after dawn. If Elwood detoured to the motel where Twiggy was waiting for him, that would explain the gap in time. Jake didn't miss his wedding, he deliberately skipped it in order to gig with the band.
It was that very gig when he robbed the gas station to pay the room service bill and got arrested the same night. And he had a fling with another woman which explains the used condom (the Mystery Woman remained a virgin until her wedding date). Either that, or said gig (plus the fling) was the night before Jake would have gotten married if the cops hadn't arrested him. The reason why Jake didn't tell his fiancée was because he was afraid she'd also find out about his infidelity.
Burton Mercer isn't a plain-clothes police detective but a private investigator who collaborates with the police.
Not only does he never wear a uniform, but he doesn't seem to carry a weapon either. Instead of showing a badge, he hands out business cards. What kind of cop has personal business cards with a phone number on them? Besides, he knows things the police don't, including where Elwood lives. He has clearly been there before, the extended cut reveals that he knows Sam, the guy sitting on the stairs, by name, and it's quite unlikely that flophouse dwellers take a cop casually going in and out kindly, especially without letting Elwood know.- Mercer is Jake's parole officer. His card specifically says "Department of Corrections" and he even says his "friend" failed to report in yesterday.
Better yet, Mercer has also been a Blues Brothers fan since before Jake was arrested.
This is why he knows where Elwood lives and the cops don't: He has stalked his remaining idol. The police managed to force him to deliver Elwood to them on a silver platter, but he doesn't really want to. He left his business card at the flophouse so that Elwood could call him — and he could warn Elwood that the police are after him, and that he had to reveal Elwood's dwelling-place to the authorities. The reason why he is so happy at the Palace Hotel Ballroom is because he's about to see the Blues Brothers' big comeback show. And the reason why he's so cheerful after crashing into the truck is because he's secretly confident that the state troopers have fucked up badly enough for the Blues Brothers to be able to escape, not knowing that every last cop in Chicago is after them, too. They're on a mission from god, and Elwood is a cleric.
Elwood is a cleric of god, with the blues and travel as domains, so he's able to repair the car with healing spells. That also explains how they maintain their suits despite never taking a break to wash them and being splattered with mud, and how the barricades in the Cook County Assessor's office last just long enough. It's literal divine intervention, but Elwood is the one directing it. Wrapping up the nazi subplot was also divine magic. Jake was telling the truth when begging his ex-fiance for mercy.
Jake wasn't throwing excuses, all those things happened for real. The orphanage mission was only their latest one. All the outlandish things Jake described were events from their previous epic quest, ultimately landing Jake behind bars.