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Silver Tool is an industrial company that offers machining fixtures, gages, custom tooling, grinding, milling, and laser engraving services.

This calculator will determine speeds and feed rates for machining operations on mill or lathes. Cutting speeds are usually given in feet or meters per minute.

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You'll want some means to guide the drill, though -- either a drill press, or a guide block as illustrated in some of the other answers, or an angle drill guide. (Just know that everyone I know who bought an angle guide eventually switched up to a drill press. Angle guides are the push reel mowers of woodworking. If you're going to drill another 20 angled holes, get the drill press, even a bench top model.)

I think Forstner bits would be the better idea for doing this though using a spade bit might be possible, if you lower it slow enough, I don't think I'd recommend it.

So to keep the bottles inverted (keep the cork wet) you have to drill down at a 45 degree angle or so. I used a 1.5" bit to drill the holes but it was real sloppy and well it just didn't go great.

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I just stumbled upon this thread as I'm also trying to make a riddling rack. I came across a portable drill guide jig which seems like it would be another potential solution, although perhaps more expensive than the wedge option if you have a drill press. Cheaper ones exist, but may not be as good.

If you make all your marks, a bit low, then start off with a small bit (maybe 1/8") and predrill to about a quarter inch and punch all the marks with it so they have a starting point for a bigger bit. It doesn't matter how deep really, if you go too deep, it will look bad. Don't go deep.

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Then while holding the drill still in motion, preferably a higher wood speed, start to tilt it. It's that easy. Have something, like a thin long nail, or something in one of the guide holes to have guide angle template.

However, I suggest you use a few jigs. I've done similar projects, and the biggest problem is that a forstner bit tends to skate around when you're dealing with angles that steep. (There's nothing for the center point to grab into until you're 1/2 way through the piece.)

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Edit: after I clicked Submit to post my answer I noticed that TX Turner posted a somewhat similar solution for the drill press at about the same time as me. The guide block I'm suggesting is different in that it's a little easier to clamp since you're clamping flat pieces together instead of wedges. You can also use any flat backer board to prevent blowout, and you can easily register it against stop blocks on your workpiece for more precise hole placement.

Drill a guide hole at the desired angle. You can cut a 2x4 at the exact angle using a radial saw and use it as a jig for the drill (see photos below).

Perfect for enlarging or deburring holes in wood and plastic. Capacity: 1/8"-1/2"

Personally, I would use my drill press. The bed will tilt to any angle and then you just clamp the board to the bed. You would need a piece of waste wood under the board so not to put the bit into the metal bed.

45 degrees is pretty steep for a hand held drill, but by starting it and slow tilting the drill to the correct angle while keeping the tip in the wood might give you something close to what you are looking for, but I'd stick with a drill press, much safer and more accurate.

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You might have to clamp this to the edge of your drill press table, so that the workpiece can hang below the table for holes further up the workpiece.

How do you make the wedge? Simple- take a square block (or make a square block from two smaller pieces) and drill a hole with the forstner bit. Then take that piece to the band saw, turn it up on edge, and slice from one corner to the other, at an angle the same as you want to duplicate.

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SO, each hole, after predrilling, enlarge your hole fullsize, keep motor running, tilt drill to proper angle, then go to depth. extraction is your best guess, either motor on, or motor off, but i think on.

then take your larger bit, and start it until it goes all the way in until the crown has gotten level with the surface, meaning, the hole is now as wide as its going to get.

If you don't have a drill press, another solution is to cut the corner off a block of scrap wood at a 45-degree angle. Use a brad point, auger, or twist bit to drill straight through the newly-cut end, and clamp it to your workpiece for each hole. If you've ever used a Kreg pocket hole jig, this is basically the same concept.