Introduction
To start off this guide I wish to clarify a few things:
1) This guide is focused on TT w/ 
Shaco
2) This guide is focused on laning Shaco.
Now that that is over with, lets get to the good stuff. I love Shaco. He is a versatile and useful assassin and one of my favorite champions to play in TT. With his fast and easy dragons, ability to backdoor, and high single target dps, Shaco is a good pick for almost any team. In this guide I will outline my favorite build, as well as a few tips and tricks for those wishing to play Shaco in both a TT specific setting as well as a champion in general.
Items - A short explanation
Doran's Blade -> 
Boots of Speed -> 
Wriggle's Lantern -> 
Boots of Mobility/
Mercury's Treads -> 
Trinity Force -> 
Infinity Edge/
Banshee's Veil/
Madred's Bloodrazor ... eventually sell your Wriggle's Lantern for a 
The Bloodthirster
Why do I build what I do? I want to say that this build is flexible, and while it is preferable to stay within the items which I have put in this guide, there are games which require situational items (
Thornmail, 
Quicksilver Sash, 
Guardian Angel, etc.) and changes in build order. A few of the more flexible choices include choosing Mercury's Treads or Boots of Mobility and the build order of items after Trinity Force. For boots, Boots of Mobility are preferred as it will lend you an extra bit of surprise to your ganks as well as chasing power for long fights. Mercury's Treads, on the other hand are extremely effective if you are getting shut down by CC, or if the enemy team is AP heavy. Moving on, which item should you build after Trinity Force first? If you are facing squishy enemies and have no lack of survivability, go for Infinity Edge... if you are facing tankier enemies/health stackers, go for Madred's Bloodrazor, and if you are getting shut down by AP champions/cc, take the Banshee's Veil first.
Situational Items:
Thornmail - this should be your reaction to AD carry monsters like 
Tryndamere, AD 
Sion, etc.
Quicksilver Sash - this is a great item to get if you're getting shut down but 1 particular bit of cc, such as 
Warwicks ultimate or 
Rammuss taunt.
Guardian Angel - this is a great item if you are getting bursted down before you can start doing any damage, but keep in mind this item is more effective during mid and late game when teamfights start to occur.
Wit's End - this item is useful for an extra bit of damage/MR, and is relatively cost effective. Feel free to replace Madred's Bloodrazor with this item if the enemy team is squishy/ap heavy.
The Black Cleaver/
Last Whisper - these items are useful against armor stackers like Rammus, 
Malphite, etc. you will want to substitute your Infinity Edge for one of these items, if you need to purchase it.
Summoner Spells
The great thing about playing Shaco is the flexibility allowed in terms of summoner spells. Because he already has a slow, hard cc, and escape mechanism, spells like 
Flash 
Exhaust and 
Ghost aren't a must-have. Personally, I prefer to use Exhaust and 
Ignite, because they, in combination with other abilities, can turn a 1v1 fight quickly to one's favor. Here are alternate recommended summoner spells:
1) Flash - this spell is for either the very offensive or the very defensive. Flash can be used both as an escape mechanism and in conjunction with deceive as a huge distance closer. In addition, you can 
Deceive over to Dragon to steal it from the enemy team, then Flash back out.
2) 
Surge - this spell works very well with Madred's Bloodrazor, and any other on hit situational items you might purchase ( Wit's End, The Black Cleaver)... there is one drawback, though. When you use Surge your champion swells in size, so using it at the same time as your 
Hallucinate takes away that uncertainty in the enemy about which clone is the real you.
3) 
Heal - I prioritize both Flash and Surge above Heal, but the summoner spell is useful nonetheless. Heal will make tower diving easy as well as increase Shaco's overall sustain in team fights.
Deceive
Deceive is your skilling priority, your burst, gank initiator, dragon ks'er, and escape mechanism. Learning when to use and when to save your Deceive, as well as your ability to maximize its damage by utilizing your passive, is what distinguishes a good from a bad Shaco. The first thing about Deceive that new Shaco players need to know is that when it is used, if your location is on the screen of an enemy (regardless of whether or not you are in a bush or obscured by fog of war), there is a smoke animation which will warn your opponents of your actions. One way I have found to cope with this is running a good distance away from your opponent (out of screen, if their camera was locked), and then Deceiveing back towards them, closing the distance with your Boots of Mobility speed buff, and initiating combat. So, when should you use,and when should you save your Deceive? I find that when I'm ganking a lane, and it the odds are in my teams favor, I like to initiate with Deceive, as it lets me close distance quickly to the target as well as deal a considerable amount of burst to start off the encounter. When I am in a 1v1 situation, however, I like to save my Deceive for either escaping or for pursuing a fleeing enemy, especially if they Flash/spin over a wall to escape.
Lastly, Deceive is a great tool for taking dragon from the enemy team, and does almost as much damage as smite.
Shiv
This spell has suprisingly long range and is a very useful slow/finishing move for a fleeing opponent... one thing to keep in mind is that to catch a fleeing enemy with low hp, deceive followed by a 
Two-Shiv Poison is very effective. Although you max this skill second, mastering its use is fairly easy.
HALLUCINATE!
Shaco's Hallucinate is his distinguishing ability, and has a plethora of uses. Here are a few tips:
1) At level 6, if you have built up to basic madreds, soloing dragon is a breeze. Simply deceive over the wall, Hallucinate, use alt+right click to pull aggro with your clone, and then position yourself behind drag to get the passive damage bonus... throwing down a jitb helps as well.
2) Backdoor/pushing! Use alt+right click to position your clone so he is tanking the turret, then wail away! Don't forget to throw down a jitb.
3) Using Shaco's Hallucinate in a team fight will give you a huge damage boost as well as create some confusion for your enemies (provided you do not have a buff/ Deceive right after) as to who the real you is, especially since the updates to the clone's realism. One thing to keep in mind is that your Hallucinate does have a cast time, so if you're chasing an enemy using it might give them time to escape, which is why activating your ultimate during a 
Jack In The Box fear or right after using Two-Shiv Poison is recommended.
4) Using your Hallucinate as an evasive maneuver is part of what separates the good from the decent. With correct timing using your ultimate can help you avoid a variety of detrimental effects, including:
a. 
Demacian Justice
b. 
Requiem
c. Skillshots
d. Charges/spins
e. Roots/snares
f. Stuns applied on hit
Laning
Laning with Shaco has its ups and downs. Until you get Wriggles, Shaco has very limited survivability, so constantly trading harass with your enemies is not recommended. Instead, going for kills in lane should be about burst... when the time is right, initiate with a Deceive/ Jack In The Box for the kill. Solo lane is slightly different. Harass here is recommended, but only with Deceive/ Two-Shiv Poison, not auto attacks... waiting until your wave is pushing down the enemy lane, with your opponent running ahead of it is the perfect strategy for landing a max dmg Deceive, then retreating. Another thing to keep in mind is the use of Jack In The Box in lane. Placing Jack In The Boxs in bushes/entrances to your lane (to prevent ganks/provide escape routes), is extremely important to your success. In addition, placing down 1-2 [jack in the box]]s and then kiting your opponent into them, while all the while saving your Deceive is a great way to get kills early game. Here are some recommended laning partners for Shaco: Sion, 
Alistar, 
Morgana, 
Swain, etc. Hard cc/immobilizes work very well with Shaco's ability to initiate w/ deceive.
Ganking
First off, here is great game opening strategy:
1) stack Jack In The Box in front of where the big minion in one of the top buff camps will spawn, 4-5 will do.
2) Your Jack In The Boxs will kill the buff/small minions with the help of auto attacks/grant you level 2.
3) Deceive over the dragon wall into top lane for fb gank, but wait for your Jack In The Box to be off cool down.
this method is the reason that I grab Jack In The Box first, and is a great game starter. However, I recommend taking at least one teammate up to guard you while you place Jack In The Boxs so that you are not ganked. If the enemy team does show up, try and kite them into your boxes for an easy fb. Keep in mind you want your allies to be gone by 1:55, lest they steal xp from the camp and thus your level 2.
Now, moving on to general ganking... Shaco is a great ganker. Boots of Mobility/ Deceive allows him to move from lane to lane in seconds, often quick enough to help turn a 1v1/2v2 fight in your team's favor during the laning phase. For this reason, map awareness and communication between allies is a very valuable asset in for any Shaco. In general your ganking should look like this: initiate w/ Deceive, put down a Jack In The Box in the direction your enemy will flee, get off your crit, Two-Shiv Poison, etc. However, you can also save your Deceive if you know an enemy has Flash/an escape mechanism or if the other members of the enemy team will join in to help their allies in which case Deceive can be used as an escape.
Dueling (1v1 Encounters Explained)
Very often in TT, the fate of a game is determined by 1v1 duel fights between both team's carries. In order to fully utilize Shaco's potential, understanding how to go about a 1v1 fight is essential. The first thing to remember is that engaging a fed enemy is never a good idea unless you know you can win. The only thing worse than not getting a kill and surviving is not getting a kill and dieing. The next thing to remember is that bushes are your friends. Here is a basic outline for conducting 1v1 fights:
1) Harass/poke: use your Two-Shiv Poison/ Deceive to get some initial damage on your opponent, but try to avoid direct confrontation.
2) Set up 1 or more Jack In The Box in a nearby bush/location (optional)
3) Initiate combat w/ Two-Shiv Poison/ Deceive (preferably Two-Shiv Poison if you have no Jack In The Box's set up for escape)
4) Kite your opponent into a bush before using summoners (if you are losing the encounter)/chase down your opponent with Exhaust/ Two-Shiv Poison/ Deceive (if your opponent flees)
5) At this point, the duel will be slanted in one person's favor, if you are losing badly, consider fleeing, but if you are at reasonable hp in comparison with your opponent, pop your [hallucinate]] before your opponent enters the bush and then use your summoners Ignite/ Exhaust, and go for the kill. If your opponent is fleeing, chasing them down with Deceive, Two-Shiv Poison, Exhaust, and Ignite should be easy business, especially with Boots of Mobility. Don't prematurely use your Hallucinate in a chase, it will do no damage if the clone cannot catch up. If your opponent flees under a tower with low enough hp to dive, use your clone to tank the tower while you close distance to your opponent. Do not pull tower aggro with a long distance Two-Shiv Poison, as your opponent may well still have Flash/the ability to kite you to your death.
Conclusion
Thank you for viewing my guide! I hope it is helpful to both experienced Shaco players as well and new Shaco playsers, and I wish you the best of luck in your games to come. I just want to remind everyone viewing this guide once again that it is tailored for TT item wise, skilling order wise, and rune wise, but many of the tips and tricks I've presented can still be used on different maps.
Here is some proof this guide works
and:
^notice that game is a 2v3
Build Guide
Discussion (6)
Greater Mark of Desolation (x9)- I use these runes because they simply lend the most dps for an ad champion out of those available. These marks also work to offset my lack of armor pen. quints and compensate for some of the damage loss.
Greater Seal of Resilience (x9) - These seals are very useful for a number of reasons. They work to remedy some of 
Greater Glyph of Warding (x9) - I prefer these glyphs over MR/lvl, but both are viable choices. Much like the seals, this extra MR helps fortify your survivability throughout the game.
Greater Quintessence of Furor (x3) - Here is where I differ from a number of 
Lethality in the offense tree. One thing I'd like to point out and explain is my choice to get 
Vampirism instead of the 
Havoc... I do this first because 1.5 bonus damage out of 100 is a relatively low buff, and secondly because the 3% lifesteal coupled with the lifesteal present on your 
