If you didn't unlock Sideshow Bob in the event, a new questline, Flaw and Order, needs to be completed before this one starts.
Flaw and Order Pt. 1Auto starts
Homer: Good news, Bart. The psychopathic killer who has dedicated his life to your death has escaped from prison.
Bart: Sideshow Bob escaped?! How is that good news?
Homer: You get to stay home from school until they arrest him.
Bart: Wow. I hope my murderer escapes more often.
Wiggum: Well that isn't going to happen. We're going to catch Sideshow Bob and put him in the most secure solitary confinement we have: The Glass Cube.
Wiggum: Nothing can destroy it, except its natural enemy: rocks.
Task: Arrest Sideshow Bob
Wiggum: Enjoy the Glass Cube, Sideshow Bob. I've never seen a villain escape from such a place.
Wiggum: Then again, I never watch the movies.
Flaw and Order Pt. 2Bart starts
Bart: Hey, I just saw Sideshow Bob running around free again.
Bart: I thought you put him in The Glass Cube. You said it was inescapable.
Wiggum: It is. But it's also really expensive. You can't believe what we spend in glass cleaner alone.
Wiggum: So we stuck Bob back in medium security. He may escape a few more times, but eventually he'll get the message.
Wiggum: Unless he kills you first. Then I guess he won't get the message.
Task: Arrest Sideshow Bob
Wiggum: Back to jail, you sidekick from Hell.
Flaw and Order Pt. 3Lisa starts
Lisa: Chief Wiggum, I just saw Sideshow Bob on the loose yet again!
Lisa: I thought you put him in a medium security prison.
Wiggum: He was really wrecking up our prison.
Wiggum: So now we have him sitting in the police station guarded by a really mean dog.
Wiggum: Actually, kind of a nice dog. We were scared to have a mean dog around the station.
Wiggum: Okay, don't give me that look. I hate it when children give me that look.
Task: Arrest Sideshow Bob
Sideshow Bob: You're wasting your time. You can't keep me in jail.
Wiggum: That's where you're wrong, Sideshow Bob. You'll never escape again.
Wiggum: I mean, really, it's exhausting. You'll be good, right?
Sideshow Bob: *MANIACAL LAUGH*
Wiggum: I'm gonna call that a yes.
After unlocking him, a new quest starts, if you had him in the event or unlock him after.
Rake It to the Limit One More Time Pt. 1Sideshow Bob starts
Sideshow Bob: Once again I'm back in Springfield. And yet, somehow it's different...
Sideshow Bob: As though it had been blown to smithereens, and then clumsily reassembled by some knucklehead with zero clue about how to lay out a town.
Sideshow Bob: But if this is a different Springfield, then perhaps I am a different Sideshow Bob, no longer cursed with the obsession to kill Bart Simpson.
Sideshow Bob: Only one way to find out: spying on the Simpsons from the bushes around their house.
Sideshow Bob: Hm. Apparently my love of creepy stalking hasn't changed.
Task: Make Sideshow Bob Spy On The Simpsons
Time: 12h
Location: Simpson Home
Rake It to the Limit One More Time Pt. 2Sideshow Bob starts
Sideshow Bob: I've been spying on the Simpsons for hours, and I still feel absolutely no urge to murder Bart.
Sideshow Bob: Apparently whatever idiot blew away Springfield also blew away my hatred.
Homer: Wait! I feel a strange disturbance in the cloud. Somewhere, someone is calling me an idiot.
Bart: That's not strange. Somewhere, someone is always calling you an idiot.
Homer: Why you little...!
Sideshow Bob: What a delightful zing by the lad. And look how nimbly he dodges his father's ape-like hands and skateboards away.
Sideshow Bob: If that's not worth an amused maniacal chuckle, I don't know what is.
Task: Reach Level 12 and Build Bart's Tree House
Task: Make Bart Skateboard
Time: 4h
Task: Make Sideshow Bob Laugh Maniacally
Time: 8h
Rake It to the Limit One More Time Pt. 3Sideshow Bob starts
Sideshow Bob: Principal Skinner, it's a brave new world, and I'd like a job at your school.
Sideshow Bob: Perhaps I could teach gifted and talented students about the Shakespeare play where the phrase brave new world comes from.
Skinner: The only thing my students are gifted and talented at is troublemaking. I have the whole fourth grade on lockdown.
Sideshow Bob: Well, I'm also highly familiar with the Federal penitentiary system.
Skinner: Hm. With you in charge, I could join my birdwatching group in its hunt for the variegated nuthatch.
Sideshow Bob: The nuthatch? An aerial daredevil of jaunty plumage indeed!
Skinner: You're also a nuthatch nut? You're hired. I just need a job reference.
Sideshow Bob: Call Cliff The Grim Reaper Franklin at this number.
Sideshow Bob: But I'd do it before Tuesday at midnight. His appeal is not going well.
Task: Make Sideshow Bob Teach at Springfield Elementary
Time: 8h
Location: Springfield Elementary
Task: Make Skinner Go Bird Watching
Time: 24h
Location: Trees
Task: Make Lisa Go To School
Time: 6h
Location: Springfield Elementary
Rake It to the Limit One More Time Pt. 4Bart starts
Lisa: What a wonderful teacher Sideshow Bob is. He has a real soft spot for teacher's pets.
Lisa: I guess being blown into a fog of atoms and then reconstituted in a world ruled by a giant sky finger really can change a man.
Bart: I don't trust Sideshow Bob. Today he tried to look past my bad behavior and reach me as a fellow human being.
Bart: What kind of teacher does that? He MUST be a phony.
Bart: And there's one last test I can do to prove it.
Task: Make Bart Lay a Trap
Time: 1h
Location: Springfield Elementary
System Message: Purchase Sideshow Bob's arch nemesis, the Rake, to continue the plot!
https://tstotopix.files.wordpress.com/2015/05/tapped-out-purchase-rakes-takedown.png
Rake It to the Limit One More Time Pt. 5Sideshow Bob starts
Sideshow Bob: I can't wait to start my day teaching at Springfield Elementary.
Sideshow Bob: I love the look of joy on eight-year-old faces as you recite to them The Canterbury Tales in the original Middle English.
Sideshow Bob: Finally free of my obsessions, I stride confidently across the playground, a free man!
Task: Make Sideshow Bob Meet His Raker
Time: 1h
Location: Rake
Task: Make Bart Laugh His Head Off
Time: 1h
Location: Springfield Elementary
Sideshow Bob: Every rake that hits me increases my rage!
Sideshow Bob: What cruel tormentor doomed me to this fate?
Skinner: I'm fairly confident it was Bart Simpson. From the fourth grade?
Sideshow Bob: Then Bart Simpson must die!
Rake It to the Limit One More Time Pt. 6Sideshow Bob starts
Homer: Bart, I just got a call from Principal Skinner. Sideshow Bob is trying to kill you again.
Homer: He says it's okay if you stay home today, as long as you get a permission slip from me.
Bart: I told you Sideshow Bob couldn't be trusted! I'll be hiding in my room.
Homer: I didn't say I was going to give you permission.
Lisa: Great job, Bart. You proved that Sideshow Bob wanted to kill you by driving him so crazy that he wants to kill you.
Homer: It just goes to show, you can vaporize people in a nuclear explosion, but you can't stop two jerkwads from driving each other crazy.
Task: Make Sideshow Bob Plot His Revenge
Time: 24h