One of the best artists to combine humor with a lot pop culture references in his work is Matt Cowan who came up with another excellent idea for a series of pop culture mash-ups that would make incredibly cool T-shirts.
Jon Snow is the most emo of the Game of Thrones characters and Princess Mononoke might be the best of what Hayao Miyazaki gave to the world.
Itchy the Killer
Combining the worlds of a TV show inside a TV show cat & mouse that hate each other with that of a manga series called Ichi the Killer.
Gimli son of Gloin is the better known half of this duo. Red Dwarf is a brilliant TV Show which is something of a science fiction standup.
The Kevin Bacon Mix Tape
Go watch Guardians of the Galaxy.
The Star Lord Bros.
Another Guardians of the Galaxy reference, combined with the two most famous Italian plumbers in the world.
Bender, one of the most obnoxious robots in the history of television, and the Ender’s Game book, which turned out to be a slightly crappy film.
Tis Nothing but a Scratch
Combining Darth Vader and Monty Python is a wonderful idea.
A combination of the delightful Peppa Pig and the Iron Man duo of Tony Stark and Pepper Potts.
These works and a lot more can be found on his Deviantart page.
For a bit more on awesome T-Shirt ideas, check out these 14 brilliant ones with Star Wars themes or these 21 T’s inspired by books.