Sunset Sail Happy Hour Pier 15; 6:30pm; $30
You’re king (or queen) of the world! Hop aboard Hornblower’s Sensation and cruise along the Hudson while taking in unbeatable views of the Manhattan skyline. As you dance to live DJ's tunes on all three of the Sensation's decks, you’ll be treated to Francis Coppola Diamond Collection wines, light bites, and Tattly’s temporary tattoo bar. And, yes, we’ll forgive you if you say, “I’m on a boat!” all night long. (We’ll be saying it too.)
Sex and the City Trivia Tribeca Taphouse; 8pm; free
Manolo Blahniks. Post-it breakups. Pee-playing politicians. If the adventures, romances and fashion choices of Carrie, Miranda, Samantha and Charlotte still feel like scripture to you, then gather your own NYC foursome for five rounds of intense trivia at Tribeca Tap House.
HBO Bryant Park Summer Film Festival: Dirty Dancing Bryant Park; 5pm; free
What could be sexier than the Catskills? Relive one of the most beloved romances of all time at this free outdoor screening. Eat your feelings with bites from Hester Street Fair—including Manousheh, Pokee NYC, Renagade Lemonade and Taiyaki.
Blake Daniel Sings Laura Marling Joe’s Pub at the Public Theater; 7:30pm; $20, plus $12 minimum
Daniel came to New York as a teenager 10 years ago to appear in the original Broadway production of Spring Awakening, then played the Young Thing in the 2011 revival of Hello Again. Now he retraces the past decade through songs by the intense English neofolk singer Laura Marling.
Bob the Drag Queen: Queen for the People Knitting Factory; 7:30pm, 10:30pm; $25, at the door $30
The take-no-prisoners drag diva hits Knitting Factory for this uproarious Brooklyn Comedy Festival show, featuring her buddies Matteo Lane, Sandy Devastation, Alotta McGriddles, Lady Bearica Andrews and Papusa Smear.
Modern Love Brooklyn x Orchard Grocer Ice Cream Social Orchard Grocer; 6pm; free
Dip into delicious vegan variations on ice cream sandwiches, sundaes, soft serve and more at this cheerful ice cream social, at which all proceeds benefitting the Ali Forney Center.
Sugar and Spice: Erotica Open Mic Night Q.E.D.; 10pm; $5
Drew Eliza and Jennifer Harmon Gersbeck welcome storytellers and performers to share their most uncensored, liberating tales at this open mic night.
Sketch Night + Live Music Society of Illustrators; 6:30pm; $20
Bring a pencil and pad to this weekly night of creative revelry, at which you'll get down to bangin' performances while sketching nude models. Between artistic streaks, you can meet other creative types over a cocktail bar and complimentary buffet. August 15's event features jazz vocalist and singer-songwriter Ming Lee.
The RoastMasters NYC The Stand; 10pm; $5-$10
Join hosts Luis J. Gomez and Big Jay Oakerson for some head-to-head competitive roasting. Think rap battle, but with more laughs and a lot less rhythm.
Brooklyn Comedy Festival Presents: Snowy Bing Bongs Across the North Star Combat Zone Nitehawk Cinema; 7:30pm; $16
The brilliant and bizarre Cocoon Central Dance Team presents their totally batshit feature film at this special Brooklyn Comedy Festival screening. Come ready for a new stoner classic courtesy of Tallie Medel, Sunita Mani and Eleanore Pienta.
BATZU! Jebon Sushi & Noodle; 8pm; $22.50–$60.50
Head downstairs to eat and drink at Jebon while members of improv group Face Off Unlimited compete in a Japanese-style variety show; losers undergo a variety of wacky punishments like electric shocks and paintballs to the chest.
Brooklyn Comedy Festival at various locations; 7:30pm; ticket prices vary by show
The city's best comics bring their stand-up, sketches, improv and more to Kings County during this week-long annual fest. Don't miss Bob the Drag Queen's "Queen for the People" Aug 21 at the Knitting Factory, featuring performances from Alotta McGriddles, Lady Bearica Andrews and Papusa Smear. The Fancy Show hits Littlefield Aug 22 with host Rob Haze and performers T.J. Miller, Liza Teyger, Roy Wood Jr. and more, while popular monthly throwdown Backfat Variety presents a special festival edition at 61 Local the same night, and dance-comedy trio Cocoon Central Dance Team's performance-art-meets-sketch-show bonanza "Snowy Bing Bongs Across the North Star Combat Zone" goes down at Nighthawk Cinema. With a lineup this stacked, the only downside is not being able to catch everything. Head to bkcomedyfestival.comand let the agonizing begin.
Joe Sharp Sings! Live! Joe’s Pub at the Public Theater; 9:30pm; $15
Twisted southern-bred sketch and improv master Josh Sharp returns to the Joe's Pub stage for this sweet night of strange song covers and goony comedy. Between renditions of D'Angelo and Adele classics, he'll be joined for bizarre banter with his Fucking Identical Twins co-creator Aaron Jackson, Talking Funny podcast host Christi Chiello and satanic cabaret genius Cole Escola. Sharp's father will be in attendance, so be warned: it will get weird.
Dave Chappelle with Special Guests Radio City Music Hall; 8pm; $99–$350
After suddenly leaving his hit sketch show at the height of popularity back in 2006, Chappelle took a break from the limelight. But now the comedian is back in full force with the mega success of two specials on Netflix. During his 14-show Radio City residency, Chappelle will play host to a variety of musical guests including the Roots, Chance the Rapper, Erykah Badu, Lauryn Hill, Childish Gambino, Lil Wayne and John Mayer.
Confidential Delilah; 8pm; free
Serve a spy look worthy of Charlize Theron in Atomic Blonde and enter this seductive live game, in which you’ll have to identify a person of interest among a group of mysterious strangers. Upon entering, you receive a complimentary drink and hors d’oeuvres, along with a dossier detailing your mission. It’ll take all your moxie to find your target in the crowd, but the potential to win $100 and a bottle of champagne makes it all worthwhile. This flirtatious arena comes from Never Sleep Alone’s Dr. Alex Schiller and her Masquerade on the Town partner, Alfredo Guenzani, so you can count on high-glamour theatrics and many chances to lock eyes with curious new mates.
Summer in the Square: Dueling DJs Union Square; 5pm; free
Fancy yourself the next Simon Cowell? At this weekly showdown, some of the city’s best musical talent—violinists, DJs, dancers, beatboxers and beyond—face off, and you choose the winner. This week features local DJs Tom Macari and B. Mills squaring off with their turntables to prove who’s the best mixer in the game.
House of Vogue House of Yes; 10pm; $10 in advance, $15 at the door
What started in Harlem moves to Brooklyn as DJ MikeQ of Qween Beat collective and MC Commentator Buddha host this spectacular vogue ball. The formerly underground, queer, nightclub dance technique has become a canonized genre. Catch the fierce competition, as dancers vogue and pose their way to winning cash prizes. All attendees are encouraged to let loose and enjoy the bar as performers show off their catwalks, duckwalks, dips, and hands.
Metropolis Burlesque Presents: Hooray for Hollywood Drom; 7:30pm; $15, VIP $20
The kinky nerds of Metropolis Burlesque hit DROM for their second annual tribute to all things BoJack Horseman. The washed-out equine ’90s sitcom star will need the help of some of the city's best burlesque artists to survive his Off-Off Broadway run. Check out acts from Sarah Lynn (Petite Renard), Diane Nguyen (Heart Crimson), Mr. Peanut Butter (Brettzo), Sextina Aquafina (Minnie Crisis) and more at this sardonic night of stripteasing.
Brooklyn Museum Music Video Night Brooklyn Museum; 8pm; $16
The Brooklyn Museum hosts a music video screening, meet and greet, and talk with New York artist Eif Rivera. Eif—who has worked with Wyclef Jean, Nicki Minaj, French Montana and Nas—shares about his life, his art,and the Caribbean influence in his work. Get there before the event starts to enjoy the two-hour happy hour and sets by DJ Hella Kitty and Hannah.
Charlie Park Jazz Festival Marcus Garvey Park; 7pm; free
Once again, the city becomes a movable ode to Bird for a weekend in August. While this fest may be named for the legendary Charlie Parker, SummerStage’s jazz program isn’t stuck in the past. This year, the 25th anniversary features boundary-pushing talent presented over four days, including tap dance virtuoso and choreographer Jason Samuels Smith, saxophonist Joshua Redman's quartet and clarinet player Anat Cohen.