Some of life's most crucial moments are marked with a beer—whether you're toasting your latest achievement or drinking away your sorrows. But with so many brews on the market today, how can you be sure you've selected the right one for every occasion? You wouldn't want to climb to the top of Mount Everest only to crack open a Lime-A-Rita.

So we decided to talk to a man who knows beers and how to drink them, founder of the acclaimed Dogfish Head Brewery Sam Calagione. We asked him to suggest the perfect beer to drink at a number of notable milestones many of us will face throughout our lives, from your first legal brew until your final fateful beverage.

What is the perfect beer to drink when you turn 21?

"A 5-year-old vintage Chimay Red," Calagione suggests. "Don't try to fool us. This isn't your first beer. Like every red-blooded American, you drank whatever beer was cheapest until you turned 21. Now that it's too legit to quit, make your first official adult beverage count—something like this big Belgian brown ale that you will always remember."

What is the perfect beer to drink after graduating from college and realizing you have no idea what you want to do with your life?

When pondering life's big questions, don't underestimate the creative power of beer, Calagione says. His suggestion: "Dogfish Head 60 Minute IPA. Like, seven of them. So many good ideas about your future are bound to come to you about half way into this session." But he also admits an ulterior motive: "Even if they don't, by purchasing our beers, you will be helping me afford college tuition for my kids, so they, too, can someday be in the postgrad position of not knowing what to do with their lives."

What is the perfect beer to drink after you just won $10,000 playing craps in Las Vegas?

"Probably a light lager from a massive brewing conglomerate," he suggests, lamenting the kind of suds still slung by most big casinos. "Vegas is getting better with venues serving indie craft beer, but you have to play the odds, and odds are somebody worked hard to make sure that a ubiquitous light beer was given to you for being a bigger winner and spender."

What is the perfect beer to drink when you're trying to impress a first date?

"Something super fresh in a growler from the best small local brewery in your area—the one that is obsessed with quality and consistency," he says. "Chicks dig quality and consistency."

What is the perfect beer to drink on your wedding day?

"Something dark and strong that has an awesome shelf life and will age as well as the world's finest Bordeaux," he says. Calagione has been a huge advocate for aging beer, a trend that is often misunderstood but can be extremely rewarding. Any beer with a big enough ABV (typically over 8 percent) is a candidate for aging, especially darker beers that don't rely on hop freshness as their key attribute. Calagione tosses out a few of his favorites: "Perhaps the Sierra Nevada Narwhal Imperial Stout, Dogfish Head Palo Santo Marron or Victory Storm King Stout." From there, he suggests you have a plan: "Buy a case of whichever one you choose and enjoy a bottle with your better half at every anniversary to see how the beer is improving and gaining complexity with every year. Hopefully, the same holds true for your marriage."

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What is the perfect beer to drink after you've finally quit that shitty job you always hated?

"BridgePort Old Knucklehead Barleywine," he says, choosing a beer with a bit of extra strength at over 9 percent ABV. "Buy a round for your coworkers and that dink of a boss you are finally getting away from. Offer a toast to Old Knucklehead. Stare hatefully at your old boss as you clink glasses. Then break the bottle and use the big chunk still in your hand to fight your way out of that cubicle maze."

What is the perfect beer to drink after the birth of your first child?

"Re Ale from Birra del Borgo brewery in Italy. Because for you, my friend, shit is about to get Re-Ale."

What is the perfect beer to drink when you've just bought a new home and you're hanging out in the empty house before the movers bring all your stuff?

"750-milliliter bottles of Cantillon Gueuze," he says, suggesting one of the world's most sought-after Belgian sour beers. "It's intense sour stuff. It's delicious. It isn't cheap, but the bottles are tall enough that if you drink four of them, you can set them up to be the legs of a coffee table that has a greasy pizza box for a table top. Bam. Your first piece of furniture. You're welcome."

What is the perfect beer to drink while trying to hide from your 12-year-old daughter's sleepover?

"Some sort of stout over ice. It will look like a soda in your pint glass." Though that trick is probably easier to pull off when you're not one of America's most recognizable brewery owners.

What is the perfect beer to drink on your daughter's wedding day?

"Surly Coffee Bender. I am about to get surly with my new son-in-law, letting him know he better always respect my little princess."

What is the perfect beer to drink right before your first colonoscopy?

"Russian River Damnation."

What is the perfect beer to drink while enjoying your retirement on the beaches of Cabo San Lucas?

Again thinking practically, Calagione suggests a beer you're likely to find down in Mexico: "Guinness Extra Stout at 8 percent ABV." Not only will that stronger beer help you get your retirement buzz on, but his selection also speaks to the often-neglected versatility of the stout. "You wouldn't think dark beer tastes great in hot climates, but does it ever!"

What is the perfect beer to drink when you're lying on your deathbed?

You've used beer to get through every moment of your life. He believes beer might even be the trick to extending life a bit further. What would he drink? "Every beer we have ever made at Dogfish Head," he jokes. "Just one an hour and just like that I get to stay alive for a few more weeks. I smell a Seinfeld marathon. Break out the chips and dip!"