"Generation X" doesn't tell me a whole lot about when you grew up as it appears to encompass a range of 20 years of births (1961-1981 according to WP). In the US (and I'll focus on the US because I think that's where the reverse application guy is from), the unemployment rate reached a peak of 10.8% toward the end of 1982, due largely to the monetary stabilization policies of Mr. Paul Adolph Volcker. In 1981 it was in the 7's and it was back down to the 7's by 1984. A bad recession, yes, but it led into an era of extended low unemployment rates (all the way down to around 5.2% in 1989) until the recession of the early 90s when it jumped back up to 7.8%. This didn't last for long, as the greatest period of extended prosperity the US has known in a long time dropped unemployment rates to the 3's, 4's, and 5's for much of the 90s. For a while there in the 80s and 90s, members of "generation X" actually came out of school with a better chance of landing a job than most graduating classes in the history of the US.
In Canada, things actually happened to be quite a bit nastier then than they are now:
http://www.tradingeconomics.com/Economics/Unemployment-Rate....
Now look at the current era. I graduated college in late 2007, at almost the exact moment hiring froze in almost every industry. By 2008, you'd be lucky to get a job if you had 5 years experience, nevermind zero. By 2009, the unemployment rate had jumped up to 10%, a level the US had not seen since the early college graduation days of "generation X". In 2010 we've seen moderate levels of hiring, but no sustained push. Now those of us who graduated in 2007 are looking at possibly a 4th year of sluggish hiring.
So again...I maintain that young humans, in general, have less humility than they should (primarily because they don't know the difference between "good" and "bad"), but this level of humility in the application process (however you can even measure that) probably varies heavily on market conditions. If you graduated college in 1981...my condolences to you. You had it rough there for a few years. But try to keep in mind that there are lots of people out there right now who are in the exact same boat.
And with regard to "being worse off than your parents", I don't think there's a young person alive in the US who isn't at least partially bitter about the massive debts your generation and the ones that came before it have left us with, all while being bragged at by older people about how amazingly humble they are. And let's also not forget that your generation isn't "worse off" than your parents if you're counting by measure of inflation-adjusted income.
Also important to note: this kid wasn't getting responses from employers after going the humble applicant route. I had the exact same problem: people just wouldn't return my calls. So if he does have a lack of humility, it's a direct result of not having a job in a poor economy.