Inside the Polo Lounge at the Beverly Hills Hotel, long-suffering actor Leonardo DiCaprio is basking in his post-Oscar glow from the night before. He holds court at a large table, seated next to longtime buddy and “Pussy Posse” cohort Ethan Suplee. Wearing a wrinkled t-shirt and baseball cap, Leo tries to keep a low profile, fending off gawkers like Yankees legend Derek Jeter, designer Vera Wang and Verdine White of Earth, Wind & Fire, while stealing French fries off of a friend’s plate. He’s got no idea that 50 feet away, Big Sean is totally geeking out. Read more…

The rapper is a big fan. He loved The Revenant and really wants to go over and give props to the actor, but he doesn’t want to look like a psycho stalker. After some trepidation, he decides against it. “I ain’t gonna bother him right now,” Sean says.

It’s 2 p.m. and the Polo Lounge is, as Sean puts it, “very lit.” Since 1941, the restaurant has been one of Los Angeles’ quintessential places to see and be seen. Frank Sinatra and The Rat Pack used it as their personal watering hole. Marilyn Monroe shacked up with her lover in a nearby bungalow. Enveloped in warm, rich wood and dark green décor, soft piano music wafts through the dining room and into a lush, outdoor garden where waifs in big sunglasses nibble on Russian Osetra caviar and tagliatelle with black truffle. “This is a level of success people dream of,” Sean muses.

He wears a grey t-shirt with Stevie Wonder emblazoned on it, dark jeans and a blue Detroit Tigers baseball cap. For two kids from the Midwest who grew up on the doughy, empty-calorie goodness of Olive Garden’s unlimited breadsticks, it’s kind of a mindfuck. “We’re probably the only people from Michigan right now sitting across from Leonardo DiCaprio or some other people who in here who got [millions] and [billions].” Sean takes a sip of pineapple and Jameson whiskey, letting the moment crystallize. “I belong here, too.”

Big Sean does belong here. In a way, his trajectory has been very much like Leonardo’s. Sean has wanted to rap since he was 8 years old. After three studio albums and four mixtapes, Sean’s finally getting his due. Over the past year, the 28-year-old (born Sean Anderson) has quietly evolved from hashtag rapper-cum-Kanye West protégé into a bona fide superstar. Buoyed by the success of his first platinum album, Dark Sky Paradise, and his headline-grabbing personal life, which yielded the Dear John banger “I Don’t Fuck With You,” Big Sean is a commercial and critical contender for the rap throne.

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