This guide is intended for someone who has never played Fiddlesticks before and wants to learn the core elements of Fiddlesticks's game play. It is intended to bring them to a playable level as fast as possible. If you are still reading this, the majority of your success as Fiddlesticks will depend on your map awareness, not your specific skill at Fiddlesticks. Below, you will learn everything that makes Fiddlesticks unique as a jungler.

Strengths

Can solo dragon at level 5
Amazing Early Game
Great Ganks
Ridiculous Base Damage
Ridiculous Sustain
3 second Fear
Can kill an adc before fear wears off in middle game


Weaknesses

CC shuts him down
Countered by warding
Item Dependant
Gank Dependant
Weakish late game (I'll explain later)
Needs the first 2 Blue Buffs

Spirit Stone is necessary to take Dragon early.

Boots are for ganking immediately after Dragon.

Spirit of the Spectral Wraith's spell vamp makes overcoming Bountiful Harvest's sustain nearly impossible 1v1 unless the enemy can interrupt it.

Enchantment: Distortion on Sorcerer's Shoes boots reduces the cooldown on Flash further, making keeping people in your Crowstorm far easier.

Zhonya's Hourglass is for team fights, as you will often jump into the center of the enemy team alone in order to initiate and your Crowstorm keeps damaging even while you are in stasis.

Go Hunter's Machete, Vision Ward, Mana Potion to start if you fear an invade or don't foresee having any trouble before level 5. Fiddlesticks is susceptible to early invades, so if you are invaded, don't fight. Simply place your Vision Ward by your Ancient Golem before the enemy team reaches it and wait nearby to try to Smite it back unexpectedly. If your team was watching for the invade, you should've been able to set the Vision Ward down before the enemy team saw you, denying them knowledge that you ever owned a ward. It is likely that the enemy jungler will try to save their Smite in order to rush to their own Ancient Golem and kill it to keep it from you, so you should have no problem Smiting your buff back.

If you want to keep tabs on the enemy jungler, buy 2 Sight Wards instead of the Vision Ward and Mana Potion.

Your Jungle order is as follows.

Ancient Golem
Wolves
Wraiths
Red
Golems
Gank top/bottom, depending on which side you on, if you can gank. (Don't wait around for a gank opportunity though. Your real goal is dragon)
Wraiths
Gank Mid if you can gank. (Don't wait around for a gank opportunity though. Your real goal is dragon)

Note* Do not take unnecessary risks before you Dragon. Dragon is your early game goal. Kills are simply secondary objectives at this point.

Note* Flash ganks are surprisingly effective. Nobody expects a level 4 Fiddlesticks to Flash right next to them, Terrify them for 1 second, and do 1/2 to 3/4 their health in damage before they can escape (ignoring your teammate for whom you are ganking.)

You should be near level 5 by this point. If you aren't level 5, clear a camp and you should be. The second you turn level 5, go back. Buy Spirit Stone, Boots (for ganking at level 6), 2 Health Potions, and Mana Potions until you have 2. You should have have some gold left over. If you have enough money to buy an Oracle's Elixir rather than a 2 Vision Wards, do so. If not, get 2 Vision Wards and a green if possible. Immediately run to Dragon.

This is the most important point in your game and will determine whether or not you are a good Fiddlesticks or a bad one.

Upon arriving at Dragon, immediately place a Vision Ward just slightly outside of the entrance to Dragon, as knowledgeable opponents might be ready for an early solo Dragon and put a ward at the back of the Dragon cage. Place your ward so it can see enemy wards both outside the Dragon cage and at the back of the cage.

Now, that you've warded Dragon, take a look around. If there is an enemy ward at Dragon, you won't want to immediately take Dragon. Instead, kill the ward and wait a bit and see how the enemy responds. While you wait, place a Sight Ward (if you have one) in your enemy's jungle to watch for enemies while you're taking Dragon. If bottom lane or mid lane is pushed, gank there and to push the lane back for a safer Dragon. If the enemies ward dragon or investigate it while you're waiting, wait for them to leave and kill their wards, waiting a bit more to see if they return before you go in to take Dragon.

If you've gotten to Dragon as fast as possible, you will find yourself at a vulnerable point in the game. Your Crest of the Ancient Golem will have worn off, but the Ancient Golem won't have respawned yet. That's why the Mana Potions are necessary. Immediately begin Bountiful Harvesting Dragon, watching your map for roaming mid or bot lanes or just a jungler heading bottom to gank. when your first Bountiful Harvest wears off, there will be a moment or two when Bountiful Harvest is on cooldown. Use Reap on Dragon and pop all of your potions before Bountiful Harvesting again in order to maximize the effectiveness of the potions. Bountiful Harvest Dragon down and Reap in between Bountiful Harvests. Your Smite does 610 damage at this point (you'll eventually remember it because you'll do this every game.) By the time you kill Dragon, you should be at 3/4 health and 3/4 mana. If you are quick you can take dragon before 7 minutes and have two dragons before 14 minutes.

Note* Make sure you know the exact second Dragon is up again so you can claim the second one as quickly as possible.

If you took Dragon as soon as you hit level 5, you'll find that it wasn't quite enough to bring you to level 6. Fortunately, you Ancient Golem should be up by now. Go clear it, healing yourself to full health with Bountiful Harvest, and go on a ganking spree. Please note, you need the second Ancient Golem in order to both reach level 6 and optimize the effect your Crowstorm has early game. Additionally, Spirit of the Spectral Wraith and Sorcerer's Shoes with the Enchantment: Distortion are optimal at this point for more effective sustain and chase. Zhonya's Hourglass is for the team fighting phase, so you do not need to own it by this point. However, building it as your third item should still be a priority.

From this point in the game, you are a ganking monster. Gank every time your Crowstorm is up, but also gank any time an opportunity arises. Your combo is Crowstorm> Terrify> Reap> Bountiful Harvest. The Dark wind is to delay flashes and dashes. You do enough damage without your ult to bring nearly any champion to half before they can escape (provided you're close enough to land your fear) by yourself. Buy Oracle's Elixirs whenever necessary and take full control of the jungle. You can 1v1 nearly anyone who lacks cc which can interrupt your drain or abilities which can lower your healing (ignite.) Only the burstiest of mages can out damage your Bountiful Harvest, and often times you can burst them down before your Terrify has worn off. Get every Dragon the second it comes up, using either Vision Wards or Oracle's Elixirs, depending on how many wards the enemy team is buying, to make sure the coast is clear.

Notes on ganking*
Always Crowstorm from a bush if you can, but if you can get between an enemy and their tower, feel free to ult onto them (especially if you have Flash up.) Remember to buy Oracle's Elixir whenever necessary. At this point you can out sustain a turret's damage, so feel free to tank a turret for a team tower dive. The majority of Adc's can't out damage your sustain at this point in the game. Keep an eye on the map and try to intercept roaming laners in river whenever possible.

As the first team fights start to begin, you role changes. Your enemies have either build magic resist to counter you or haven't, depending on their role. You must identify the squishiest high priority target (mage or adc) and assassinate them at the beginning of every team fight.

Hide in a bush or behind a wall when both teams gather. Pick your target and Crowstorm as close to them as you can, Flashing if you must in order to get right on top of them. Terrify> Reap (to silence surrounding teammates who might cc you)> Bountiful Harvest your target. If they were squishy enough, they will be dead by the time your Terrify wears off or soon after. Use Zhonya's Hourglass if the enemy team tries to focus you down immediately, making sure the full damage of your ultimate gets off.

This method is most effective early in the team fighting phase, when most champions do less damage than you can sustain. You must make full use of this window of high effectiveness, making sure your teammates follow you into the fray and take full advantage of the chaos you have sown. Chances are that your ult has brought any nearby squishies who weren't your target down to 1/2 health and any tanks down to 3/4 health. It should now be a 4v5 with the enemy team severely injured and lacking their highest damage dealer.

Note* your ult has a shock factor to it. It is likely to make your opponents panic. They will either waste all their CC on you or run in a blind panic. Either way, if your got a good ult off and your team dashes in to clean up, the enemy team will lose the team fight.

You should try to get every dragon as soon as it's up throughout the game and never delay getting them unless there is a team fight going on.

Note, that by the time you start to finish your 4th item, Fiddlesticks starts to level off. when you start to feel this change occur, you should start to change your play style more to the late game style described below, becoming more like a support and letting other carries take over. Once this change occurs, you should still build new items when available, but keep a slot open so you can always carry wards.

Unless you are getting CC'd, Rylai's Crystal Scepter is your best 4th item. The extra health helps ward off burst and the slow makes escaping your Bountiful Harvests harder. However, if CC is an issue, your 4th items should definitely be Banshee's Veil, after which you should probably buy a Rylai's Crystal Scepter anyways.

If you don't If enemies build MR, build Void Staff. If your team is magic heavy, build Abyssal Mask.

At around level 15 the weight of carrying the game starts to shift to your teammates. You have your core build, allowing you to assassinate the adc for sure (and the mage if they built no MR,) but the tanks and off tanks have built enough resistance to weather your initial Crowstorm. Not only that, but your Bountiful Harvest peaked at level 9, so now your ability to survive has diminished relative to the enemies's increase in damage. If you have done well enough early game, your team should have no problem taking over the role of damage dealer and carrying you to victory. If you haven't, you'll find that while you still deal a ton of damage, the enemies can now out damage your sustain, often killing you 1v1. Your Terrify is now your most powerful weapon, as the three second fear is still long enough to take out the squishy targets and secure many kills, but right now you are far better of playing like a support, assassinating the adc when you can and spamming fear at all other times. Buy a lot of Sight Wards and Oracle's Elixirs and watch for out of position enemies you can kill easily.

Note* If the enemy team is immensely squishy, you should still take a more aggressive role. It's only the tanky bursters or bursty tanks you should be fearing.