If I'm in the skill-monkey role, I figured that I would play a rogue mildly inspired by Captain Jack Sparrow. While I'm not certain of the race (although human is most likely), the character is a former member of a pirate crew who owes a debt to a powerful sea creature and has thus decided to spend the rest of his life safely on land. After all, adventuring is a lot like piracy, right? He disguises himself due to a bounty on his head, but is terrible at it and tends to find himself laughing and taunting during fights rather than lying low.
I have two possibilities that have sparked my interest if I end up in the tank position. One is to play a half-orc fighter on the path to be a battle master; however, he has a scholar background and has no real experience with actual fighting. Although he will have the natural ability and knowledge, he will find the actual fighting to be both a bit of a let-down from his adventurous imagination and a little less hygienic than he would prefer. This idea probably comes from a web comic I once saw where a half-orc has a doting orc mother and a bookish human father who are both caring parents that take interest in and encourage his passions.
The other tank option is a halfling barbarian. His backstory is less happy as he and his shire were the victims of a wizard gone bad who pressed them into slavery and worked experiments on them for a generation or two (a bit darker even than the ravaging of the Shire from the end of The Return of the King). A group of adventurers saved them, but the wizard escaped. This character spent his entire life undergoing experiments and hardship, and he looks up to adventurers in general (and the band that saved him in particular) as role-models. Meanwhile, he seeks the wizard who tortured him and his village, and the power and abilities to get his revenge.
I also have an idea for a cleric if a healer is needed for the party, but the nature of his backstory (and the fact that some of my group members might come across this post) makes it so I don't want to share this particular idea at this time. Meanwhile, I have yet to come up with a mage-type class that I really like; although, I did recently learn about hexblades, and I think it would be interesting to be bound to a weapon like the hilarious (and possibly evil) black sword from the Stormlight Archive series.
I haven't decided on accents or voices for these characters yet--well, except for the pirate (which would be my standard pirate voice as I can't pull off a Johnny Depp impersonation). I'm not sure which one I would want to play more if given a completely open choice. Honestly, I kind of want to find out what might happen to all of them.