My top two rated cigars that I've smoked to date have been:
2009 H Upmann Mag 46
Tatuaje Pork Tenderloin
The H Upmann I had in DBall's BTT and it was the highest rated cigar I had. At 9.9 (or 99 if you want to rate it on the 100 point scale) it was almost perfect in every way except some very minor draw issues at the beginning of the cigar that cleared up.
The Pork Tenderloin I didn't review or rate, but everything about it was amazing. From the beautiful wrapper, the perfect draw, and the amazing flavors, if I had reviewed it I'm sure I would've given it as close to if not a perfect score.
Unfortunately for both of these cigars I only had the one H Upmann for the review and then I only have a 5'er of the Tenderloin
The other cigar that is my higher-end, go-to, highly rated, and consistently enjoyable stick, is my box of VSG Sorcerers

I fear I'll go through these too quickly though so I only have been smoking one a month or so.