Have you tried any of Speyburn, Tamdhu or Glen Garioch? They’re all about $25 and good whiskies.
Always Jack Daniels.
Otherwise Maker’s Mark.
It could have been me who said it.
So I’ll say it again - in the $30 range, Marker’s Mark bourbon and Famous Grouse scotch.
As a $30 alternative, how about two bottles of Sunny Brook and a bag of weed? 
You don’t graduate past Jack Daniels, you may become too pretentious and snobby to drink it just cuz frat boys do, but Jack Daniels is still the best. 
If your bag of weed costs less than $ 30 for a gram it’s not worth smoking.
I second Maker’s Mark and Knob Creek.
And that means it’ll go great with the two bottles of Sunny Brook!
But that breaks your $ 30 budget.
I can go with Knob Creek, or Maker’s Mark both are great whiskeys. I will toss one more name into the hat however. Try a bottle of Jim Beam Black. Compared to the KC or MM it’s a bargain also.
I’d recommend a good single-malt Scotch, such as Glenlivet or Dalwhinnie. (So long since I’ve shopped for such, though, I don’t know if you can get a bottle for $30.)
N.B.: Warn all your friends not to touch your Dalwhinnie!
Before or after they pre-diluted it? 
JD is decent enough stuff, but when I said “graduated” I meant in the sense of “Self, I’ll be there’s other stuff out there worth trying!” much like people go from guzzling Bud to exploring the nuances of microbrews.
As for “snobby” - there’s a big bottle of JD at home, right next to the big bottle of MM.
On a whim, I hit the liquor store on the way home and picked up a bottle of this! It was $25!
I came in to mention Woodford, just a great bourbon and the bottle is cool so you feel all special while your drinking it out of the paper bag on the corner (just me?).
Jameson’s is good - mild, slightly sweet, bit of a vanilla flavor. I drink it neat or on the rocks, but it’s also good in Coke.
Also - seconding the Black Label. Yah, there’s better scotch out there - but this is good stuff, and worth drinking. 
I’m here to add my voice to the Maker’s Mark chorus.
The $25 Spayburn is turning out to be quite good, despite the face that the cork snapped on me.
Note that I mainly drink Irish whiskey, and what follows are two of my recommendations within the sub-type.
**Tyrconnell **is an excellent Irish whiskey. I consider it to be one of the more cost effective whiskies, in that it costs around $15 less than, say, Connemara, but is less than 33% not-as-tasty (if that made sense). A bit of a strong start, with a nice nutty, slightly sweet back.
Since Black Bush has already been mentioned, I’ll point out its similarly-priced but sweeter cousin, Bushmills 10 year. Very smooth with a caramel back. An absolutely wonderful whiskey. So much so that I’m sitting here wondering why there isn’t any in my cabinet right now!
For $30, if I want a smoother Irish whiskey, I go for Bushmills 10. If I want something a bit bolder, I go for Tyrconnell. Can’t go wrong with either.
I don’t buy whiskey very often, but my last purchase (which was months ago), was Tyrconnell, partly because I enjoy it so, and partly because it’s a bit rare in my area (whereas the Bushmills 10 grows on trees), so when I see it at the store I have to suppress the impulse to purchase it for fear of it not being there the next time I visit.
They’re both excellent.
As a postscript, I will heartily recommend Connemara if you ever feel like splurging ($45-50 a bottle around here). Peppery, with a nice smoky smooth back. Best whiskey I’ve ever had, but then I’ve only ever had one bottle; it is on the expensive side.
Bulliet!! Sweet and vanilla, sooo yummy.
I think you’ll find that the Bushmills 10 Year Old is definitely above the US$30 mark. I was going to say the same about Tyrconnell but looking on the BevMo.com site I see that they have it for US$29.99 as list price and actually have it on sale for US$26.99, which means I need to go tomorrow and see if they have any back in stock. In regards to your esthetic assessment of both whiskeys I am in full agreement, though the Tyrconnell is very much of different character than most Irish whiskeys, like a lighter Islay Scotch rather than the smoother, peat-less flavor of most Irish whiskeys. Good stuff, though, especially at the price.
Stranger