Having revealed who some of my (current) top 5 preachers are, it seemed appropriate to explain my criteria for choosing them - afterall it is more than a little subjective.

1. Having something to say and saying it - sounds obvious but some preachers can burble on for 10/20/45 minutes and say nothing at all.  I don't have to agree with or like what is said, but I like to hear something! 
2. Consistency/dependability - I suspect anyone can deliver one good sermon, but a good preacher will usually be good.  Anyone can sometimes deliver a lousy sermon, doing this does not automatically stop them being good.  If you're going to get into my good preacher list, I need to hear you a few times to decide.
3. Plays to their strengths in terms of style/delivery etc. - this doesn't mean they never take risks or try new things but on the whole stick to what they are good at.  Indeed, the best preachers do sometimes take risks that don't quite work and then have the guts to admit it.
4. Do their homework (at least most of the time) - you can tell if someone has put the work in or not.
5. Use notes or a script!  Not just because this makes me feel better because I do, but because most of the time these are the people who keep on track, have something to say and say it.  I have heard some great 'notes free' sermons but it is not in my book a sign of the preacher's greatness.

When selecting my greatest sermons, the criteria are fewer and even more subjective.  Not surprising then that the list changes frequently and consists of relatively recent sermons.

1. It speaks to me in some way, challenging and/or comforting as I need, the best do both at once.
2. It is competently delivered (if not, I am likely to get too hung up on other factors to hear what is said)

My current favourites are (in no particular order) ...

• Stuart Jenkins - 'Mary and Martha' c. 2002
• Anne Phillips - 'Shift Expectations' and 'Jesus asleep in the fishing boat' both 2003
• Best experimental sermon - Sean Winter 'heave offerings and other odd OT texts' (not what it was called but hey) c. 2001
• Best special service sermons - Ernie Whalley , Partnership Valedictory Service 2003 and Peter Grange, building closure and thanksgiving service 2005. (btw Baptism/Ordination/Induction sermons are de facto special so permanently in my remembered list)
• Best big stage sermons - Ex-President Jimmy Carter at BWA in Birmingham who had the courage to name what other speakers had skirted around over Baptist fall outs and issues.  (He said it wasn't a sermon, I'd say it was.) Anna Mafie (Italian BU) at Baptist Assembly 2004