The pair downed a whole lot of booze and played drinking games in the hilarious segment.
In a hilarious segment for Late Night, the pop superstar joined the charming host at the Jane Hotel's bar in New York City, where they kicked things off with shots and then downed some beers before even getting down to the drinking games. A source tells ET that the two for a little over tow hours.
First off, Seth played bartender and whipped up some cocktails based on the names of some of Rihanna's biggest hits -- including a drink called Under My Rumbrella, which is just straight rum, poured over rum balls and rum raisin ice cream, topped with a handful of tiny paper umbrellas, and We Found Veuve in a Hostess Place, which is Veuve Clicquot champagne garnished with an entire hostess Twinkie.
The pair soon moved on to a series of drinking games -- where they didn't get any less free-flowing with the booze. First, Seth quizzed Rihanna by showing her paparazzi photos showing her in various outfits and asking her to name the event she wore them to.
After that, they moved on to pick-up lines, and Seth got the songstress to help judge his game. Seth's been married for years and shares two children with his wife, Alexi Ashe, and it shows from his less-than-stellar flirting skills.
Asking Rihanna to ring a bell as soon as his pick-up line proves too cheesy, a clearly tipsy Seth comes on with a number of lines that have Rihanna ringing the bell almost immediately.
His pickup lines included "Hey, you look like a lady who was also underwhelmed by the Game of Thrones finale," and, "Excuse me, are you the girl from Battleship?" The latter of which caused Rihanna to just straight up walk off, leaving Seth to ring the bell on himself.
Wrapping up their fun day, Seth asked Rihanna to use some of her new Fenty Beauty products on him and the results of their drunken makeup session was Seth looking like one of "the blue people" from Avatar (according to Rihanna), before the host serenaded her with a hilariously tone-deaf rendition of her song "Work."
Here's a toast to the wonderfully fun Late Night segment, and to the possibility of getting more installments of Day Drinking in the future.
Late Night With Seth Meyers airs weeknights at 12:35 a.m ET/PT on NBC.