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Not Updated For Current Season
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**** tier lists. I've played Fiddlesticks on and off since Summoner Level 1 and there is something about him that makes him incredibly fun to play. You can win 1v1 fights against most champions that don't have a form of strong CC and you can focus down enemy carries in teamfights while healing yourself greatly.
Your allies will love you. Most importantly, your enemies will fear you. Just how it should be.
2. Jungle Route
Blue Golem (SMITE Golem here) -> Wolves -> Duo Golem -> Wraiths (SMITE Big Blue Wraith here) -> Lizard -> Wolves etc.
If they lack a jungler, steal their blue when yours is beginning to fade, position yourself behind their golem next to the trees and Drain, use Flash to escape if you are detected, it is relative risk free.
Go back when you see fit. Rinse repeat jungle pattern. Don't risk Dragon until you have the Blasting Wand, he's much harder to kill now.
Don't waste time with Mana pots on Fiddle. Get Ward for Dragon and Health Pot for crutch situations (Saved me more times than I can remember.
Fiddle can punish overextenders hard. Around level 4 you can pull off the basic combo:
Run in from behind, try to time your run in to avoid the minion waves, and Terrify -> Dark Wind -> Drain. This works best if your laning ally has some CC to stop them while your Drain gets it's full tick.
At level 6 and above the fun begins. Squishies will perish. Crowstorm -> (Flash if neccessary) -> Dark Wind -> Terrify -> Drain. Notice Dark Wind before Terrify this time, as the higher level Dark Wind now will bounce more so you will want to use it earlier.
4. Late Game
Never initiate teamfights. Aim to come in about half way through the teamfight when they are sure they've won an easy 4v5. Aim to land in as many people as possible, Dark Wind the main bulk of enemy champions, then quickly Terrify and begin draining their squishy carry. Don't be afraid to off-tank with Drain.
The only exception to this rule would be if they are pushing a tower and you have allies to back you up behind the tower. Crowstorm over the trees and use Drain first to keep yourself alive. A good location to Crowstorm from is the wraiths to defend mid tower, your teamfights will follow your iniation and Drain should keep you alive unless they are fed. Avoid doing this if they have lots of hard stuns.
PROTIP: If you want to win a 1v1 fight but Terrify/Drain is not enough, chip them down a little with Drain, then bait them towards a brush. As soon as you enter the brush, Crowstorm back on where you just came from, in their direction. By the time they enter the brush thinking you are still running away, your Crowstorm will have been half cast and they will have very little time to react (I should point out here, don't try this against characters with a hard CC, such as Taric). Finish the combo with Terrify -> Drain when your Crowstorm lands and reap the rewards. Throw a Dark Wind out too if you are near an enemy minion wave.
Play smart and remember your Drain does not make you invincible. You are a Tanky Mage because you are always in the middle of the battle. Always take this into account and don't be tempted to stack AP. Follow the guide and let me know how you do!
Please don't downvote without commenting. Enjoy!