In Bedazzled, the protagonist, Elliot, starts out as one. Definitely Played for Laughs when he asks to be "the most sensitive man in the world."
Deconstructed and ultimately subverted in The 40-Year-Old Virgin. While Andy may fail at one night stands and short-term relationships compared with his more outgoing and lecherous coworkers, guess who's the first to sustain a healthy long-term relationship and get married?
Jocelyn: Please, men say that, but when you get to know some of these men who complain the most, you find out they're not as nice as they think they are.
Stanley Ipkiss from The Mask. He grows out of it by the end of the film, where he learns how to still be a nice guy without being a pushover.
The tongue-in-cheek book Nice Guys Don't Get Laid.
No More Mr Nice Guy is another, more serious self-help book where Dr. Robert Glover covers the 'Nice Guy' syndrome in detail. He explains that being a Nice Guy is not a good thing for you or your intended loved ones, repeatedly points out that acting like a self-centered jerk is just the opposite extreme, and generally advises that balancing your own wants and needs against those of other people is the key to happiness.
Live Action TV
iCarly: Freddie invokes this by trying to prank order a fishy pizza to his teacher's house in front of Carly. When the pizza place calls back, he panics and runs away.
Actually works in iStage An Intervention when he pulls a prank on Sam after she pulled one on her. Carly is impressed, but Freddie lacks the confidence to follow through and try to ask her out.
There's an episode of The IT Crowd that plays with this in all kinds of weird ways. Roy tries to prove that "all women want bastards" by making a fake profile on a matchmaking Web site for a mean alter ego (it starts with "Shut up!"), and when he gets a response from a woman he actually quite fancies, he goes on a real date with her but has to pretend to be the bastard his profile made him out to be.
Friends: Chandler - probably the nicest character on the show and the one who gets the least action dating-wise - lampshades on this, quipping that someone saying he's a nice guy means I'm going to be dating a chain smoking alcoholic and complaining about them to you.
Averted later on though, when his extremely attractive best friend Monica (whose its hinted he's had feeling for, for years) falls in love with him and they're Happily Married long before the rest of the gang.
Subverted on Girl Code. While the first part of the "Bad Boys" segment says that All Girls Want Bad Boys, by the end of the segment the cast agrees that Nice Guys usually wind up better off in life so they're the ones that girls SHOULD be going for.
Cobra Starship has a song called "Nice Guys Finish Last", but it has a fairly tongue-in-cheek tone, and (given that it appears on the same album as "Pete Wentz Is the Only Reason We're Famous") really shouldn't be taken seriously.
Green Day's "Nice Guys Finish Last" predates the song above, though it's not a Trope Namer by any stretch.
The romantic version of this trope tends to be heavily enforced on "geek websites." Go into just about any geek-centered internet forum or website, and you're bound to see people complaining about being too "nice" to get a girlfriend.
The song "Mr. Cellophane" from Chicago. Though in this character's case, he was actually married...to a fame seeking woman with low standards who dumped him after she was done using him.
Girls With Slingshots Jim goes on a tirade that "nice guys never get laid" to four perfectly normal guys who are getting laid. They are not amused.
Unfortunately this would have worked better if the normal guys had not been actually bragging about getting laid in front of Jim.
Something Positive has Mike declare this, as he whines about acting like a girl's friend, only to have her fall for some better-looking guy who actually asked her out, rather than the creepy guy who was pretending friendship so he could get something out of it.
XKCD presented a comic featuring a nice guy going over his modus operandi.
Nice Guy: When you have problems, night after night, I'll be there for you. Selflessly. I'll tear down the jerks you date and wait for you to realize how good I am for you. That only I will ever understand you. You won't want to hurt my feelings, and I won't ever hurt the issue. I'll tell myself it's because I "value our friendship". Bit by bit, I'll make you depend on me. You'll think about how long it would take to build this kind of connection again. And in a moment of weakness, and loneliness, you'll give in. It'll feel comfortable and natural. You'll quietly revise your definition of love and try to be happy. And sometimes you will be. Only the wistfulness in your gaze and the tiny pause before you say "I love you" will hint that this wasn't the ending you'd hoped for.
Online comedian Jenna Marbles rants about this saying in her video "Why Nice Guys Don't finish last. She points out that a lot of nice guys who can't get dates fail in their pursuit because they tend to go after the wrong types of women. The Cheerleader has nothing in common with the nerd, so she shouldn't be seen as stupid or a bitch for not wanting to date him.
"Nice Guys" by Nigahiga, Kevjumba, and Chester See is actually a subversion. In the music video, the guys go to a class where they learn that they must act like jerks in order to get women. However, they soon realize that acting like jerks actually makes girls hate them, and being nice is what really works.
Specifically, the song on it's own plays it straight, the music video that goes with it subverts it.
Doug Walker discussed this one in a commentary, stating that while he knows he gets taken advantage of and is called a pussy for having such an apologetic nature, the Good Feels Good feeling is still worth it.
A podcast in The Art Of Manliness explores this, noting that the "nice guy" is not always as nice as he thinks, often believing his own good nature allows him to act passive agressively. This is especially when it comes ot the myth of All Girls Want Bad Boys.
An episode of the Baby BluesAnimated Adaptation focused on this. When Rodney asks Darryll for advice on women, Daryll tells Rodney he was a nice guy in high school, but if he [Darryll] could do it all over again, he'd be the biggest jerkass ever because he never got the girl. Rodney takes this to heart and starts acting this way, and sure enough, girls fall all over him. At the end, Darryll finds out the bad boy who competed with him is now working as a janitor, and stops thinking this way.
Subverted in that one of Rodney's co-workers, who makes more money and works less than Rodney, admits to being like the janitor.
The Powerpuff Girls "All Chalked Up'' likewise used a variation of the "aggressively nice" option when Him tries to use Bubbles naivety to his advantage.
While it might have been misquoted, in terms of career, some studies have found that it's true, with people considered more disagreeable more likely to get hired and make more money in their lifetimes. Some have boiled it down to basically if a person is a little bit of a Jerk Ass, they're more likely to A) feel entitled to a promotion, raise, etc. and B) actually ASK for it. When applying it to a person's love life, however, it gets a little more tricky, with a big problem being most people tend to confuse "Nice Guy" with "Doormat."
For some women, a man who takes charge, is very confident (even if borderline egotistical), and is aggressive in their persuasion tend to be more appealing since it makes them look more manly.
People who are more aggressive in a relationship (not physically, mind you) of any kind tend to be taken more seriously and will usually have their demands met when they ask nicely but firmly. People who don't stick up for themselves in an argument or go along with what everyone else wants in order to make them happy are usually viewed as weak willed and are taken advantage of. Naturally, there are times where you have to be a nice guy, otherwise you will be seen as a rude jerk, so for some people, the balance between being nice and being firm/aggressive can be tricky to maintain.
And, of course, the nice guy will be less likely to actually ask a girl out because he doesn't want to come across as intrusive, while the "macho jerks" have no such qualms.
A common rebuttal to self-identified "nice guys" who use this argument as a thinly-veiled cover for Entitled to Have You is that being nice— genuinely nice, that is, not "nice"— is a minimum qualification, not the be-all end-all. In other words, okay, let's grant for the sake of argument that you're nice. What else do you have going for you? Being intelligent, or funny, or emotionally balanced/open, or insightful, or fun to be around, or romantic, or well read, or passionate about causes, or a thousand other traits are all much more interesting than the basic human niceness of, say, holding the door open for someone or listening to them talk without being an ass to them.
Leo Durocher, manager of the Brooklyn Dodgers, has often been credited with first saying this phrase. But what Durocher actually said, before a 1946 game with the New York Giants was: "The nice guys are all over there. In seventh place."