From the OP's detailed description, I'm inclined to believe that these jokes contain an element of maliciousness, the type of practical jokes where the victim may not spontaneously burst out laughing. The OP suggests that we call the person who performs these jokes; a jerk, a s.o.b, a creep etc. Therefore I suggest the following term
a. A playful or mischievous act; a prank.
b. Mischief; prankishness. Often used in the plural.
reckless or malicious behavior that causes discomfort or annoyance in others
- A person who performs shenanigans.
Apparently, the term shenanigans in the US is considered slang,
and the phrase “call shenanigans” is used in some regions of the US.
Shenanigans are activities which are intended to be mischievous and
playful. Pranks and jokes, for example, are both considered to be
shenanigans. This term is also sometimes used to refer to deceptive
activities which cause harm, irritation, or upset, and people might
use the term “no shenanigans” in the sense of “no funny business,”
meaning that such activities will not be tolerated. This term is
especially common in the United States, which may be its country of
origin, although no one is certain. [...]
The meaning of the word is also quite slippery, as
it is used in a number of different ways, and its adoption as a slang
term has further clouded its meaning. Curiously, people rarely use a
singular form of “shenanigans.” Apparently a single shenanigan is
simply unheard of. Shenanigans can have more sinister implications, however. Some people use the term to describe confidence tricks and other deceptive activities which are linked more with wrongdoing than fun times. The victims of these sorts of shenanigans may be embarrassed, humiliated, or injured, and they run the risk of losing money as well.
In some regions of the United States, people use the term “call
shenanigans” to talk about calling someone out for questionable
activity. Someone who suspected that he or she was being bilked at an
auto repair shop, for example, might say “I call shenanigans,”
suggesting that some sort of deceptive activity or wrongdoing might be
occurring. Practical jokers may also find the tables turned on them by
victims who call shenanigans, putting an end to the joke by indicating
that they have seen through it.
Source: Wise Geek