For this mission, you have to deface all of the sheriff's posters around town. You should deface them in the order given by the game. Their locations are marked in the map as well for your convenience. Next, you have to steal Toothpick's lollipops. It is located out in the open at the town hall.
Finally, head to where Toothpick's banner is hanging and tear it down. You can do this by climbing the electric pole east of the steel bridge. Knock off the clips to complete the job and obtain the jailbird costume.
Jail House Blues
You'll be controlling Bentley for this job. Head to the first location and zoom in to take a photo of the prison tower. Head to the next location to take a photo of the munitions dump. Finally head to the lookout point by the cliff to take a photo of the prison's back wall.
The control will switch over to Sly. Use the iron ball to destroy the wall. Jump down to the ground and use the ball to smash the prison door open and free Kid.
Now you have to make your way to the exit. You need to push the prison carts out of the way. You can also bust the nearby doors to destroy objects inside for additional coins. Jump across the spiky pit and crawl under the hole by the wall to go around the cart. Push it to the pit afterward. Now exit and push the platform for Kid to reach the other side.
Before crossing the rope to regroup with him, destroy the crate covering the outhouse to reveal a mask behind.
In the next area, push the three coal carts to help you cross the gap and reach the other platform. Push the cage there using your jailbird costume to open the gate. Regroup with Kid and push the melting pot he's on. Just time your push to avoid the flames. You can do this by pushing him as soon as the fire jets stop.
Continue until you reach the high-tech floor trap. Equip your jailbird costume and press R2 to ride the ball. Avoid the TNT barrels and the security lights until you reach the pressure plate needed to deactivate the trap. Continue outside to learn you new objective. Before moving forth, look to the left to find a mask behind some barrels.
Refer to the video below to easily solve the mechanism puzzle.
In the next area, ride the iron ball and make it to a safe spot then push the cage to create a pathway for you to cross. Be careful when riding the ball since you can fall off to the spiked pit below. Before you can push the cage in the middle, you have to turn off the trap. There's a pressure plate in the corner to disable it. Now have Kid put the TNT on the back wall to complete the job.
Cooper for Hire
Follow Toothpick to the mine but stay out of sight. He occasionally stops and looks around so make sure to move from cover to cover while keeping tail on him. After reaching the mine, the control switches over to Murray. Take control of the gatling gun and keep the scorpions away.
After the gatling gun sequence, you have to hack the system again. The mechanics are the same as before. The only new code that will be introduced is the speed code. Just follow the instructions to successfully defeat the security codes, get past obstacles and destroy the firewalls.
The control will now switch to Kid. His gun cane can be used to shoot targets from afar. Keep shooting the vault door to open it. Head out and shoot the switch before moving forth. Kill the enemies ahead and open the next vault door using Crackshot. You'll be taught how to execute it.
Ride the track and avoid the obstacles and electric charges along the way. Just jump to switch tracks and continue forth as necessary. Once you've reached the end of the track, take out the enemies then make your way to the upper level. There, you'll find another mask.
Continue fighting your way through the path until you reach another vault door. Open it with Crackshot then ride the tracks again. Once you arrive in the next area, fight your way again through several enemies until you reach the vault door. Aside from the vault door, there are two crates you can destroy with Crackshot. Destroy them both to reveal another mask behind them.
The last train track and shoot the doors to open them. Job complete!
After entering the saloon, you have to control Bentley to serve sarsaparilla to the rowdy patrons. Miss three times and your “supply” in the lower right hand corner will be depleted, failing the job. Be mindful of the number of glasses some patrons make.
Once the control switches over to Sly, cross the beams and stay out of the floor to avoid detection. Be careful of the security light as well. Once you've reached the casino sign, smash it open with your jailbird costume's iron ball then continue inside.
Once in the casino, don't enter the crawlspace yet. There's a mask on top of the wagon in the middle. You may want to take out a couple of roving guards to avoid detection.
Enter the crawlspace and cross the beam to reach the next platform. From there, push the pot in the middle using your iron ball and be careful not to be spotted by the security light. jump on the railing and grab unto the circular neon sign on the wall
In the next phase, you have to control the RC car through the vents. You can shoot the hostile spiders that you encounter and boost through the intervals of the ventilation fans. Once you've reached a fork in the road, take any of them as they will lead to the same vent. Continue until you reach the end of the vent to complete the mission.
Head to the canyon to chase Toothpick and to rescue Carmelita. Ride the tracks then take out the targets across to remove the obstacle. Head to the next point and destroy the targets again, including the TNT barrels along the way. Protect the coach until the obstacle in the next track gets removed. Head to the next point and close the flaming exhaust pipes by shooting the valves. Don't forget to take out the TNTs as well.
Use crackshots as often as you can then manually shoot the targets to make things faster. Continue doing this until you successfully rescue Carmelita and complete the job.
For the first part of the mission, you have to shoot the enemies and obstacles along the way. After getting past the first gate, you'll have to stay put and take out the enemies from above. You can shoot the dynamites lobbed at you as well. As Kid Cooper, head up then cross the wire to the other platform. Cross the first floor trap and take out the guard along the way. Destroy the next obstacle using crackshot then shoot the button to disable the trap. Clear the next area then pull the lever to remove the gate and regroup with Carmelita.
You'll be controlling Carmelita again. Shoot the TNTs in the water then continue clearing the path and protect the barge until you reach the next platform. Have Kid circle around the turbine and make your way up. Clear the area of guards then use the crates to avoid the floor traps.
After hopping to the second crate stack, you should be able to see the button there to power off the floor trap. Pull the lever next to open the river gate. Slide along the pipe to reach the next platform. Before regrouping with Carmelita, go down the vertical rope to the side which leads to another mask. After getting the mask, hop on the boat.
Have Carmelita blow up the TNTs on the river again and continue defeating more targets ahead. After landing to the next platform, continue up and open the gate. Head inside to find Sly and the gang. Defeat the guards and quickly use crackshot to shoot the four locks and open the cage. Job complete!
Grand Key Larceny
In this mission, you have to defeat three henchmen in the Toothpick Appreciation Festival to get the keys needed to divert the train tracks.
For the first game, you have to defeat 20 coyotes to face the champ. Once the champ goes in, land a few attacks then run to avoid getting damaged. If you take damage, just take out the small fries for them to drop health ups. Avoid getting surrounded and keep moving to win this bout.
In the next game, you'll be controlling Sly. You have to avoid the obstacles and make it to the finish line before the time runs out.
For the last game, you have to beat the high score using Carmelita. The “running” target and the vulture are worth more points so prioritize taking them out. The normal targets are worth two points while the invalid targets are worth -1. Just shoot as many valid targets as you can reach the required points within the time limit.
Operation: Gold Digger
Head to the back of the van to find an explosive dispenser. Stomp on it to get a barrel then throw it to the magnetic clamps to free the van. Next, control Carmelita and fight your way on the train. Once you've reached the terminal inside the crate, the control will switch over to Bentley.
Destroy the crate using Bentley's bomb then hack the terminal.
After the hacking sequence, you'll now control Kid Cooper. Head inside the next train car. Inside, you have to step on the elevated stacks to avoid the floor trap. There's a mask behind the locked crate to the first left but you can't reach it until you disable the whole floor trap. Destroy the crate using crackshot then shoot the button to remove the laser barrier ahead. Continue forth until you find the second button. Shoot it to disable all the laser traps.
Make your way to the next train car and destroy the first crate. Head there and turn to the right to find another crate with a button. Shoot the button to make the laser barrier move. Cross the barrier and turn to the right. There's another mask there but just like before, you have to disable the floor trap before you can get it.
For now, jump to the next platform then destroy the two crates behind the barrier. Shoot the button across then cross the moving barrier. Finally, shoot the last button to disable the trap. Don't forget to run back and grab the mask. Destroy the last door with crackshot and the gang will grab the remaining gold. Crawl unto the pipe until you reach the next train car.
After the scene, you'll have to face Toothpick. For the first part, equip the jailbird costume and ride the ball. Destroy the floor trap generator and hit the valves to blow the whistle. Once he becomes a giant, evade the whirlwinds he sends until he gets dizzy. Once he's down, approach him and smack him with the iron ball to send him to the furnace. While he's trapped, continue smacking him to regain a bit of your HP and deal damage.
For the second and third phases, he'll throw more dynamites, send multiple floor traps (quickly switch to your costume and ride the iron ball) and send more and faster twisters. Continue repeating the same process until you defeat him.