Headscratchers: I Now Pronounce You Chuck and Larry
Aside from all of the other reasons that are listed below, the entire premise of this movie is stupid because that's not how life insurance works.
First of all, when one signs up for life insurance one can name both a primary beneficiary and contingent beneficiaries. In the event that the primary beneficiary (in this case, Larry's wife) dies, the contingent beneficiaries (likely his children) would receive the monies from the insurance policy should Larry die himself. Any insurance broker worth their salt would've explained this to Larry and his wife at the outset, and this wouldn't have even been a problem.
Secondly, I don't know of a single major life insurance firm that only allows you to amend your policy when you have a major life change. That's stupid. Most policies are revocable, which means you can change your beneficiaries just because it's Tuesday if you want (because who would actually pay money for a life insurance plan that you could only change at major life events? That's what life insurance is for! How many times do you expect yourself to get married or have your spouse die?). Even if he had an irrevocable policy (in which the insured - Larry - and the primary beneficiary - his wife - are considered co-owners of the policy), you can usually change or add beneficiaries at any time with the consent of the primary beneficiary...and in that case Larry could've done whatever he wanted, since his wife is dead. A quick Google search can turn up all of this information.
Thirdly, even if Larry had, stupidly, decided to only put his wife as the primary beneficiary and not put his children as contingent beneficiaries AND this insurance company has a stupid rule that only allows you to change his beneficiaries during major life events...his wife is dead. He technically HAS no beneficiary anymore. So the insurance plan should've allowed him to add beneficiary(ies) at that time because he no longer had even one.
Fourth - let's assume that for some reason Larry has not put his children as secondaries AND his life insurance firm is really so stupid as to not let him change his beneficiaries, despite the fact that he now has exactly zero. ''It wouldn't matter." In the event of his death, his life insurance policy would go to his wife, as the policy states. Since his wife is dead, it would go to his wife's estate, and any assets to his wife's estate would most likely go directly to his children - or at least to their designated legal guardian, which is most likely Chuck anyway, if Chuck is - as Larry stated - "the only person that [Larry] can trust."
And fifth, even if none of the above conditions held...he could've just canceled the life insurance plan and got a new one with a different agency. There was absolutely zero reason to enter into a sham marriage with his best friend. I mean, I know it's an Adam Sandler movie, but they could've come up with a better premise than this completely threadbare one.
What exactly was stopping them from claiming to be bisexual? It'd pretty much get rid of all the problems with Chuck having sex with any woman in sight.
More importantly, why did they need to act anti-female? No Bisexuals would account for why they would need to pretend to not be attracted to women at all (heck, the best way would have been for Chuck to be the typical Lady Killer In Love, only the "lady" is his life partner Larry, who's still got If It's Not You, It's Not OK for his late wife), but to be actually disgusted by an attractive female just because she's wearing very little clothing, especially Chuck, whom the investigator was trying to out as "straight"? It's not like the "Sorry, lady, you're really hot but I love my husband" excuse couldn't work, and if it didn't, that would have been enough evidence to declare the whole case against them invalid due to bigotry (assuming they had enough money to bring it to the courts, which they did at the end of the movie).
They're straight guys operating on mainstream assumptions about sexuality and gay culture, such as "there are no bisexual men" and "gay men are disgusted by women's bodies". A LOT of people thinks these things are true, and it's not like they took a course on human sexuality before they started their little ruse.
The entire premise of this movie is weird. Since when do you have to love someone to get married? Yes, that's the normal reason these days, but their reasoning of using it merely for their own personal gain is how marriages worked for ages. Is love really relevant on a legal level?
Well yes, actually. For example, when immigrants apply for green cards/citizenships/whatever based on a spousal relationship, the government demands evidence that it is a "real" marriage, i.e. one based on love, rather than a marriage for personal gain. And if they aren't convinced, they can assess a fine of $250,000 or five years in prison. The government stance on love marriage versus "sham marriage" is quite clear and unequivocal. This has the side effect of exposing the rampant bigotry in laws against gay marriage...at least to anyone who isn't blinded by personal prejudice.
Actually, love is only one criterion by which a marriage can be considered genuine (for the purpose of immigration). The most important factor is whether the couple have a genuine desire to build a future together. Arranged marriages, for example, are not usually based on love but can pass immigration scrutiny.
While that's certainly understandable and valid for immigration marriages, what about for people who are already citizens of the United States? In that case is love relevant on a legal level?
Okay, so... You've got arranged marriages where at least one and sometimes both people have American or dual citizenship. They have literally never met prior to the days leading up to the marriage ceremony. And the court still uses "you don't actually want to have sex all the time with just each other, so you don't love each other, so your marriage is fraudulent"? Even if the court still insisted that you can't get married without being in love (unless you have it annulled), I should have liked to have them watch Denny's "marriage, non-sexual love, legal and economical benefits, yadda yadda" speech on Boston Legal, and have the whole case thrown out due to biased judge if they still stuck to their original argument (or moved to something completely different). (Context for non-Boston Legal watchers: Denny and Alan, both males, get married under a Massachusetts license because they're already Heterosexual Life-Partners and Denny doesn't want to mess around with inheritance taxes or the loopholes in non-spousal power of attorney. He brings up my anullment point and says that refusing them marriage is just a sexuality-flipped version of refusing gay marriage.)
Not to mention, there is no shortage of straight people—both natural-born citizens of their home country—who marry for insurance benefits.
How the heck are they revered as gay icons at the end of the movie? At what point does faking a sexual orientation, manipulating the system, and trivializing love for the sake of financial security = a proud moment in the history of gay rights?
Probably because (sham though they were) they were open about it, participated in gay society, and emboldened two coworkers to come out of the closet and changed their workplace into a gay tolerant one. I mean, they did fight/suffer the gay predicament despite not being gay, and positively changed the system. That earns them some get out of jail point fractions/sympathy, anyway.
Although they could get a point for changing their workplace, the other points are pretty achievable for any gay person who's a bit active in the community. Remember that the LGBT community is an extremely active one that has achieved loads of improvements for their members in the past 20 years. Why Chuck and Larry would be icons with this in mind is a real headscratcher.
Oddly enough, that makes sense in retrospect to me. For some reason though, it makes sense in real life and not within the context of the movie. Something about being a "phony" making all the good deeds not count. It's like that part in Ratatouille where Linguini reveals the rat was doing the cooking. Like, sure, he just brought relevancy and popularity back to the restaurant, invented new recipes, won over old enemies and generally brought the whole kitchen back from the dead, but aside from Collette, apparently no one cares about all the good stuff because it wasn't completely legit. (sorry if I'm derailing with the example)
Truth in television. It's believable that straight allies would get more respect (even from a fraction of the LGBT community) that people who are actually queer.
It bugs me that the premise of the movie required complete idiocy on the part of the lawyer. The two were being prosecuted for fraud, but fraud requires an attempt to steal or otherwise defraud the plaintiff (in this case the city). However, at no point did Jessica Biel's character mention that there was NO THEFT of city funds or benefits occurring, as all they wanted was to change the beneficiary of the life insurance, a benefit which existed prior to the "marriage."
You underestimate the greediness of insurance companies.
Chuck also has at least two women hanging around him who think he's pretty great. Why couldn't he just persuade one of them to marry Larry for a month or so? That way he's still helping Larry out, and they don't have everyone on their case.
Larry also wanted someone he could actually trust to look after the children in the event of his death. If he had married some random chick, we can't say for sure how she would have treated them.
Why exactly were the Heteronormative Crusaders protesting at the ball? I mean, in the 2000's. In New York. New York, the San Fransico of the East Coast. The scene of the Stonewall Riot, and birthplace of the moder LGBT movement. A city that has at least 100 gay bars. Those protestors must be really busy covering all of them, and really lucky that no-one had clocked them out before.
I think the movie is absolutely horrible, but to play devil's advocate; the group of protesters are obviously based off the Westboro Baptist Church, who are shameless enough to protest a gay ball in a city that liberal, and actually instigate people to attack them so they can sue. What the movie failed to show you is that the second someone throws a punch at them, they're filed with an assault charge, but we couldn't have Sandler suffering consequences like that, could we?
Ok, Question: The trial scene for these two guys seemed to have gone pretty well, and everyone was totally convinced that they were actually gay. They were even about to kiss! Then Dan Aykroyd storms in and declares that they are actually straight and...they just give up? What? As far as we see, Aykroyd has no evidence whatsoever to expose the two of them except his own word, and after everything that has *just happened* with the interviews in court and everything, it seems very unlikely that anyone (except Buscemi) would have actually believed him without proof. So why do Chuck and Larry just give up right then, when they could have still gotten away with it? Even if they are tired of the ruse, they've already put so much effort into it up till then, and neither one of them want to go to jail, or lose the pension benefits thing. So why give so easily?
The MPAA told the producers of the film that if they ever showed a gay couple kissing on screen (SCANDALOUS!) they'd give the film and R rating. In-universe, Chuck and Larry are blatantly disgusted at the idea of actually having to kiss another man (which has pretty telling implications of its own) and were likely looking for an excuse.
What are the telling implications of it? That people don't like to kiss someone in a romantic/sexual fashion if that someone doesn't align to their sexual preferences? Would you be huffy if a gay man said he didn't want to romantically kiss a woman? Or if a lesbian didn't want to romantically kiss a man? It can be assumed that they weren't talking about a chaste peck on the cheek or something.
The "telling implications" are in-universe. If you saw the scene, Chuck and Larry made it abundantly clear through their body language that the thought of kissing each other disgusted both of them, so the jig was starting to be up before Aykroyd even stormed into the courtroom.
Out-of-universe as well. "Not like" or "not want" is one thing. These two looked like were about to eat some dung. Because you see, faking being gay is ok, but actually doing something that might imply they're gay is vomit-inducingly horrendous.
At that point things had gotten pretty damn ridiculous anyway. They could easily have told Buscemi to go screw himself (and would have been well within their rights to do so, a public display of affection isn't exactly evidence one way or the other as someone running a scam wouldn't hesitate at that point) but the movie was more interested in making a cheap gag and running around in circles rather than doing something actually funny yet semi-accurate for the legal system.