Event 1: Novel Writing
The work of a professional novelist is grueling, often a silent war against ones own thoughts. The winner of this event is the one which can write the best quality novel within their soul-crushing six month deadline.
The reigning International Man of Mystery is already a published author, although it's more of an endorsement piece than a novel, but certainly events of his life could probably be published as fiction and do well. But will he be able to distract himself from swinging and fighting Dr. Evil long enough to finish within the deadline?
The head of the Schroedinger band is intimately familiar with novels, being inside the bodies of fictional characters more or less her entire adult life. It's an open question whether she can adapt this knowledge into the writing process however.
Event 2: Mass Arson
Because some people just want to watch the world burn. The goal is simply sheer volume of destruction, with the caveat that only things which are on fire and burn at least part of the way down will count towards the final toll.
Strong Bad, lord of the emails, probably wants to burn things a least. But can he actually accomplish such a thing intentionally?
Rikku is more of a kleptomaniac than a pyromaniac, but she's probably proficient in combustible fuels at least.
Event 3: The Substitute
The most thankless of professions, the substitute teacher. Presented with a 3rd grade classroom, contestants will be judged on their ability to maintain order and present a successful lesson plan.
T260G isn't really human, but that can be a blessing when dealing with small children. She has a lot of knowledge to draw upon, although whether that translates into understanding how to engage developing minds with the material is hard to say.
The Invisible Woman is a mother to two, although thanks to time travel and alternate dimensions and such that's more like direct, hands on mothering with one kid half time. Unless one of them was retconned as someone else's kid, it can be hard to keep track. Anyway, no one doubts she's got the maternal instinct, but teaching one kid isn't the same as teaching thirty.
Event 4: Battle of the Bands
Our contestants will divide into teams of four, based on the stereotypical structure: Vocalist, Guitarist, Bassist, and Drummer. Each band can organize themselves into the four roles as they see fit. Winner will be judged not on technical competence, but on ability to work a crowd and get them cheering.
Our first band is The (10th) Doctor, The King of All Cosmos, Benjamin 'Don't Fuck With The' Sisko, and Lilka 'Lacking an Epithet' Eleniak. Sisko is out of his element in the rock band configuration, but isn't unfamiliar with music in general. The rest are fairly alien and occasionally clumsy, but certainly The Doctor can rock his charisma when he needs to, so who knows.
Their competition is Giselle, Rich Uncle Pennybags (aka Monopoly Man), Wile E. Coyote, and Luca Blight. Giselle is a certified Disney Princess, with the downright magical vocal ability that implies. Which may or may not translate to rocking the house. And god knows with the rest of them. It'll be interesting at least.
Event 5: Competitive Eating
Pack it in! For simplicity, we'll be using one of the classics of the medium, the hot dog. Put away the most food to collect your victory!
The humble Slime fills in the first slot. Ubiquitous monster of various Dragon Quests, it's small, but also made of gelatinous ooze that's probably all digestive material or something. Not to be underestimated in this competition.
Carmen Sandiego seems entirely out of her element here. She's a classy master thief, not a big eater. Still, perhaps some sleight of hand to 'steal' the hot dogs will get her through?
Short Form
Novel Writing: Austin Powers (Eponymous) vs Maya Schroedinger (Wild ARMs 3)
Mass Arson: Strong Bad (homestarrunner.com) vs Rikku (Final Fantasy X)
The Substitute: T260G (SaGa Frontier) vs Sue Richards (Fantastic Four)
Battle of the Bands: The 10th Doctor (Doctor Who), King of All Cosmos (Katamari Series), Ben Sisko (Star Trek: Deep Space Nine), and Lilka Eleniak (Wild ARMs 2) VS Giselle (Enchanted), Rich Uncle Pennybags (Monopoly), Wile E. Coyote (Looney Tunes/Merry Melodies), and Luca Blight (Suikoden II)
Competitive Eating: Slime (Dragon Quest series) vs Carmen Sandiego (Eponymous)