I want you to sit down for this, because a revelation like the one I'm about to share might cause you to collapse from shock and I would hate to bear the blame for your bruised tailbone: In order to make bread pudding, you'll need bread.
What you're looking for is 8 or so ounces of bread, which will yield you between 4 and 5 cups of cubed-up bread. You can go out and buy bread—a loaf of it, preferably a baguette, will probably do—or you can use an existing loaf that's perhaps gone a touch stale. This is a good use for stale bread. Panzanella, the Italian bread-and-tomato salad, is another good use for stale bread, but this is a series on baking with booze, so we'll have to set our pal panzanella aside for the moment.
Speaking of that booze, which in this case is bourbon, here's what you're going to do with it: Measure out 2 to 3 tablespoons of it, and pour it over a third of a cup of dried cherries. Or dried cranberries. Or even over some of those absurdly tasty dried blueberries that they have at Trader Joe's. But whatever you do, you are NOT to pour that bourbon over raisins because raisins are nature's boogers and they have no place sullying the good name of bread pudding.
While those dried cherries are soaking away, grab a very large bowl. It must be quite large, that bowl! Because you're going to put a lot of cubed up bread in it, you see. But I'm getting ahead of myself.
The first thing to put in that very large bowl are three eggs. Grab a whisk and give them a light beating. If that hurts you more than it hurts them you can go on and tell them that. It's OK, you're a gentle soul and people love that about you.
Since you'll not want the eggs to live a lonely, solitary life go ahead and introduce them to a cup-and-a-quarter of milk and a tablespoon vanilla extract. You'll be nervous and hope that the date goes well, which is to be expected, but I promise you it will end well for everyone involved. Especially you!
Those things, lovely though they are, do need a bit of help, flavor-wise. Go ahead and add a half-cup of sugar, a half-teaspoon ground cinnamon and a quarter-teaspoon of salt. You are also welcome to add a quarter-teaspoon of ground nutmeg or ground clove or allspice or pumpkin pie spice, if you've got those things in the house and feel like adding them. You are also welcome to skip that part. Whisk all of these things together.
But back to that bread, because it's finally time to cube it right up. Half inch pieces are ideal here, but as you may have gleaned from all the 8-or-so-ing I did earlier, bread pudding is a pretty forgiving recipe. Unlike most baked goods, bread pudding can be made with -ishes. As in, four-ish cups of bread, cut into half-inch-ish pieces, and so on. Which is nice, because it also means that you can quaff a fairly decent amount of that bourbon while you're pulling this thing together, and by all means please do so, without worrying about fouling up the bread pudding because you were too drunk to cope with precise measurements.
By now, 30 or so minutes should have passed and those cherries you had soaking in bourbon should be all drunk and bloated and maybe hiccuping? Lushes, every last one of 'em. Grab a strainer and hold it over the bowl with the milk and the eggs and the flavor things; pour the cherries into the strainer and let all that bourbon go into your very large bowl, giving it a quick whisk to get it acquainted with its new friends. Now put the cherries back in the bowl from whence they came and set it aside for just a sec.
Now it's time for the cubed bread to go for a lovely bourbon-y, milk-y, egg-y swim. Gently toss the bread in, gently stir it about so that it becomes gently coated with the bourbon-y, milk-y, egg-y mixture. If the egg gets upset because you treat the bread better, remind the egg that you love them both equally. If it will help you to feel better, you can quietly take the egg aside and tell it that the bread isn't as tough, and therefore you need to provide it more coddling. The egg might respond by storming off in a huff about how it's the one who should rightfully be coddled, but it will come around by dinnertime.
Once the bread is nicely coated and the egg has recovered from its temper tantrum, pour the whole shebang out into a greased baking dish. An 8-inch one, if you've got it. Now scatter the drunken cherries over the top of the breadstuff, and give them a light smooshing down so that they get all nestled in and cozy. Cover that all up with tin foil, and put it in the fridge for 30 or so minutes. Maybe catch a quick nap to snooze off some of that bourbon? If you oversleep that's OK too—the pan of soaking bread can stay in the fridge for up to four hours.
When you're ready to bake the thing, take the dish out of the fridge and let it come up to room temperature while the oven preheats. 350°F will do it. Now get your hands on a pan that's larger than the one into which you've put your bread; it should have an edge of at least 2 inches, because you'll want to fill it with an inch of water and then put the smaller baking dish inside the larger baking dish. Oh! That foil should still be on—bake the bread pudding for 20 minutes while covered, then take the foil off and bake it for an additional 10 minutes. It's done when a knife stuck in the center of the pudding comes out clean.
If you would like, you may also make a bourbon syrup which can be drizzled over the top of your finished bread pudding. To do so, combine one tablespoon of bourbon with one half cup of sugar in a small sauce pan. Bring that all up to a simmer, stirring and stirring and stirring until the sugar has dissolved completely. Once it has, lower the heat and stir in a tablespoon of butter until it's melted and nicely incorporated. You could make a double or triple batch of that stuff for use on ice cream or chocolate cake or a lover's nipples. But those are just mere suggestions.
Once the bread pudding has cooled a bit, go ahead and serve it with some of that bourbon syrup you made, or maybe even with some vanilla ice cream if you've got it, or you could just shove your face in it because bread pudding is so totally face-shovingly great. Just blame it on the bourbon.