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Donald Glover is at his favorite L.A. coffee shop, flirting with a curly-haired barista. It’s a sunny after­noon, and Glover, the 27- year-old costar of NBC’s Community— the strangest, smartest, funniest sitcom on TV—is sipping his mocha latte and charming a girl who, considering her location (hipper-than-thou L.A. ’hood Silver Lake) and profession (she might as well have a tattoo that reads don’t bother), should be uncharmable. And yet here she is, smiling like a love-struck schoolgirl.

Give Glover this much—the dude’s got swag. On Community he plays Troy Barnes, a dim-bulb former football jock who, over the course of the show’s two seasons, has evolved into a sweet, lovable dork. Meanwhile, the real-life Glover has gone more or less the other way, from an awkward social also-ran to a cool kid at the Hollywood lunch table. A multi-threat talent who got his first gig writing jokes for Tracy Morgan on 30 Rock while he was still an undergrad at NYU, then transitioned to acting, he’s quickly become a what-can’t-he-do prince of postmodern comedy.

“Thanks so much,” Glover grins at the girl, dropping a $10 tip. Yet the move isn’t necessarily as ballin’ as it seems. Today, you see, he’s on Maxim’s dime.

Flush with the proceeds from selling intern Steve’s kidneys, we’ve given Glover a simple mission: Take 848 of our hard-earned dollars and blow them however he sees fit. My job here is to track the spending and get a glimpse into the late nights and fast times of a rising star. For now he’s keeping his plans secret, but he admits one thing: “Most of it is going toward alcohol.”

Sufficiently caffeinated, we climb inside his black BMW and head to the day’s first stop, his friend Ludwig’s recording studio. In addition to his acting talents, Glover raps under the name Childish Gam­bino (he’s like a more self-conscious Lil Wayne: clever, neurotic, off-the-wall funny), and his must-hear mix tapes are about to be joined by a new EP. This spring he’s hitting the road with his IAMDONALD Tour, featuring stand-up comedy, special guests, and performances with a live band.

The song he’s recording today is about a wild New York night out, where “everyone wants to hang out with you and you get drunk and make out with people and don’t remember stuff.” It also includes our new favorite pickup line: “Have you ever made out with a Gap ad?” (Glover was one of the faces of the Gap’s 2010 holiday collection.)

Glover moves fast. After two takes and a quick pizza refueling—he tips the delivery guy $22—we’re en route to our next spot. On the way he runs through his backstory. Glover grew up in Stone Mountain, Georgia, the son of a postal-worker dad and a day-care-manager mom.

A self-described “black nerd,” he loved skateboarding, No Doubt, and Star Trek. After graduation he headed to NYU, where he formed a sketch-comedy troupe called Derrick Comedy and got Internet-famous with viral videos such as “Bro Rape.” His improv work at the famed UCB Theater helped land him the 30 Rock gig, but he quit that dream job after three years only to score another one days later on Community. Now the kid who used to entertain his class with a Lamb Chop puppet has an ocean-view home and drinks single-malt scotch in designer suits.

Speaking of which: It’s time to shop. We pull up to a hip boutique called Confederacy. He drops $165 on a shirt for a female friend.

Thenhe zeroes in on a pair of red leath­er high-tops.

Price tag: $91

Glover: sold.

Up front a cute shopgirl rings him up. Glover tells her about his mission today. Then he decides to take a shot. “So,” he says casually, “how much would it take to get your phone number?”

“Sorry,” she says. “I have a boyfriend.”

“Oh?” says Glover. “Well, how much would it take for that not to be the case?”

She laughs. She says they actually met once before. Does he remember her name? He doesn’t.

“I remember yours,” she says. “Donald Glover.”

“Not fair!” Glover says. “I’m famous!”

She laughs, then jots down her number. It’s now 6:30, and we’re not due at the next stop until eight. What to do?

Down the street, Glover spies a nail salon. His eyes light up. “Have you ever had a mani-pedi?”

I have not.

Glover grins. “We are so getting mani-pedis,” he says.

Ten minutes later we’re sitting in vibrating massage chairs as two Vietnamese ladies attack our bunions. “Awesome, right?” Glover says. “I dated a Filipino girl for three years. We’d do this every week.” We start talking about girls, and he asks if I’m seeing anyone. I am not.

“Oh,” he says, “we’ll fix that tonight.”

Our toes sufficiently de-gnarlied, Glover pays the bill—$16 each, plus a $40 tip—and we head back outside. It’s time to party.

Glover has arranged to meet some pals at a nearby tequila joint. His plan is to buy out the bar so all his friends can drink for free. The actor Danny Pudi, who plays Troy’s best friend Abed on Community, will be there, and a few of the Derrick Comedy guys, too.

But at the last minute Glover adds a new, awesome wrinkle: “I think,” he says, “I’m going to tweet this.”

As Tracy Jordan would say: twist!

For all the love he gets in prime time, Glover might be even bigger on Twitter. Under the handle @DonaldGlover, he posts a steady stream of hilarity and odes to girls who “#cangetit.” He was also the driving force behind the #donald4spiderman campaign, an unsuccessful yet widespread attempt to have the next Peter Parker played by a brother. How better to thank his legions of followers, he says, than by inviting them to party? And so, at precisely 9:11 p.m., he delivers this tweet to 141,342 of his closest friends: “Me and @dannypudi are at Agave on Vermont in LA. Open bar for an hour (for my fans) starting…NOW!”

The first girl arrives in less than 10 min­- utes. Her name is Melanie; she’s a student. She was doing homework when she saw the tweet and bolted to the bar. More fans trickle in—including Brandon, who went to elementary school with Glover but hasn’t seen him in 15 years (“Holy shit!” Glover says)—until pretty soon the place is packed. Glover is posing for cell-phone pics left and right; at one point he disappears, and I find him outside rapping on a fan’s phone to her friend who couldn’t make it.

Meanwhile he’s taken a shine to one of the waitresses. “I’d like to buy you some flowers,” he says. “What’s your favorite?”

The waitress thinks. “A posie? I’ve never seen one, but my last name is Posey.”

“OK,” he says. “I’m gonna tweet, ‘Someone bring me posies, and I’ll give you $40.’¿”

Sure enough, 45 minutes later, a guy bursts through the door carrying a huge white bouquet.

“Posies!” Glover shouts, and the whole place cheers.

It’s pretty awesome that a few clicks on a smartphone can result in this kind of party. It’s also pretty awesome that Glover signed up to spend his night with 60 or 70 of his superest superfans.

“This might be one of the last times in my career I can do something like this,” he says, and if that’s true, he seems really glad that he did. And then, sometime around 11—a.k.a. margarita number five—things start to get a little crazy. There’s a commotion behind the bar: It seems Glover, drink in hand, is slowly making his way up a wooden ladder that leads to the top of a giant wall of tequila. In his red hoodie and jeans, he even looks a bit like Spider-Man.

The bar goes wild. When he reaches the top, he turns to face his adoring throng.

“Everybody!” he shouts. “I want you to make out with the person next to you!”

As a few people obey, Glover scans the room and spots a girl he met earlier, standing next to her brother. “Hey!” he yells at her. “Make out with your brother!”

“No way!” she laughs.

“I’ll pay you $50 to kiss your brother!”

¿ A chant goes up in the crowd: “Kiss! Your! Brother! Kiss! Your! Brother!”

Glover tries again, louder this time. He’s dangling 20 feet in the air, his middle finger raised in jubilation. “Kiss him! Kiss your fucking brother!”

This is what NBC used to call must-see TV.

Meanwhile, Pudi is at the foot of the ladder, repeating a mantra of his own: “This is not the weirdest night ever. This is not the weirdest night ever…”

Ultimately—and certainly for the best—the kiss never happens.

After a while Glover is ready to call it a night. As he says his goodbyes, his hand entwined with the waitress’, I’m reminded of the rap from earlier, about going out, hooking up, and loving life. I’m struck by two competing realizations: one, that was totally tonight, and two, that’s totally every night.

Sometime later there’s a tap on my arm. It’s a girl. “Hey—you’re the guy writing the article, right?” she says.

As it turns out, Glover had one last surprise in store. At some point during the evening, he’d posted another message on Twitter: a photo of yours truly, along with the words, “Trying to get [me] a girlfriend. Girls, please.” What can you say—the guy’s a giver. I look around for a minute, scanning the bar for those red high-tops. But, like a true superhero, he’s already long gone.

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