Hey, hi, hello. It's me, Dave, coming correct with a little explainer.
While there is no platonic ideal of an Oddball question, the following is at least somewhat representative of the kind of sports trivia question we like to ask and the way we like to ask it:
This question is about Chicago and shutouts. Take the jersey number of the Blackhawks' shutout leader and subtract the number of fingers on the throwing hand of the Cubs' shutout leader. The result is the jersey number of a pitcher who joined the White Sox for a half-season late in his career. This pitcher ranks 13th in shutouts for the first team he played for and 2nd for the second team he played for. Who is he?
To answer this question you don't need to do all the steps, but you need to do at least two.
1️⃣ You need to know, guess, or figure out that the Blackhawks' all-time shutout leader is Tony Esposito, who wore #35.
2️⃣ You need to know, guess, or figure out that the Cubs' all-time shutout leader is Mordecai "Three Finger" Brown, who had 48, but, more importantly, had three fingers on his right hand due to a farm equipment accident in 1888.1
🧮 35 - 3 = 32
🤔 So, who wore #32 for the White Sox for a few minutes towards the end of his career while also playing for at least two other teams and ranking high on (at least) those two teams' respective all-time shutout lists?
✅ Steve Carlton, whose 16 SHO place him 13th on the Cardinals' all-time list and whose 39 SHO place him 2nd on the Phillies' all-time list.
So, yeah, all of the preamble was to get to Steve Carlton.
We write questions the way we do because:
- we think layered questions are more interesting
- we like mixing up the variables (shutouts! fingers! jersey numbers!)
- we like using multiple sports in the same question
- other reasons
In short, Oddball questions are extended of the kinds of things we ask each other. We met in a Toronto Blue Jays fan group on Facebook when I was living in Southern California in 2016. Jonathan would post trivia in the game threads. His questions were involved, interesting, and challenging. I sensed a kindred spirit. A little while later we started doing this thing where we would text each other sports trivia questions apropos of nothing. That's been going on for almost ten years now.
TL;DR Oddball is sports trivia for people who like sports, trivia, and sports trivia. They're fewer and farther between than you'd think, but we know 'em when we see 'em.
Postscript:
1 Fun fact learned while double-checking the date of the accident on Wikipedia: Mordecai Brown was referenced in F. Scott Fitzgerald's This Side of Paradise.