I did a fuckass-long (official measurement) report about my family history in Junior Year of Highschool, and it actually turned out to be moderately cool.
On dear Mama's side of the family, we have a dynasty of good 'ol fashioned Texans that were involved in the oil business, war supply, and banking-- a long line of wealthy people that very conveniently ended two generations back from me. Grandpa was an obsessive stock market gambler, and we all know how that particular avenue turned out. Generations of wealth went up in smoke, the ranch was sold and all hands were laid off, and the unfinished house I grew up in was the result of grandpa running out of money to pay the builders.
On good ol' pap's side of the family, however, things are a bit more dramatic. Dad was born in Vietnam to a South Vietnamese Colonel and a government official's daughter, but grandma's lineage is probably the most interesting. My ancestors used to support the french during their occupation of Vietnam, and through that I can trace a (distant) relation to Vietnamese Royalty.
Of course, the French don't control Vietnam anymore. This is because a lot of stabbing and shooting happened.
Starting at my grandma's dad, there is a hyper-combo of four generations of ancestors being either assassinated during the french reign, or executed for supporting the french after their fall. I have a bloodline of being fuckin' murdered, but grandma has pictures of them before they died in their fancy outfits so it's alright I guess.
Cons of Being in My Generation: $0, not being an upper-class bloke.
Pros of Being in My Generation: Not being assassinated/executed, not losing the family fortune.