I swear, my watchers are getting sick of my elder scrolls fan-art. ( Also this took me a lot of time..)
: WANING SPOILER: ( lol)
The way you join the thieves guild in Oblivion is well. It's not boring.
You either read a poster of the gray fox ( The leader at the time) ask a beggar about him. or get a note from a dark elf when you go to jail for you know... Um.. "Taking" Someone's Carrot or sweetroll. ( Because the Chime in Elder scolls are horrible).
You have to go somewhere and do the contest to "Take" a journal. If you win you get into the thieves guild!
Armond ( The Redguard in the artwork) (C) Bethesda Game Studios
Artwork (C) Me/Bonnieart04.