Brooklyn on Screen: Moonstruck Brooklyn Historical Society; 7pm; free
This is so meta. Watch a film set in Brooklyn Heights, in Brooklyn Heights. The screening begins with an introduction from Slate’s Kristen Meinzer and Newsday’s Rafer Guzman, after which you can kick back with a Brooklyn Brewery beer and bask in Cher's glory.
Whiplash Upright Citizens Brigade Theatre; 11pm; free
This always-packed show, hosted by Leo Allen, features the city’s best up-and-coming comedians. But it’s the surprise special guests—Chris Rock, Louis C.K. and David Cross have appeared—who keep audiences hooked.
Drake + Future Madison Square Garden; 7pm; $45–$180
Two of the most influential voices in rap right now grace the house that Billy Joel built—er, plays all the friggin’ time—with this four-night stretch at Madison Square Garden. Expect to hear cuts from last year’s team-up album, What a Time to be Alive (unavoidable viral hit “Jumpman” is a shoo-in), and plenty from Drake’s latest LP, Views.
Famous Friends Rochelle’s; 8pm; free
Rochelle’s brings the party (and the laughs) every Monday night with free stand-up comedy from a list of rotating comedians, plus all-night happy hour deals, including $5 beer and shot combos.
Punderdome 3000 Littlefield; 8pm; $8, at the door $10
Jo Firestone and her Rodney Dangerfield impersonator father, Fred, host this beloved competition, in which the first 18 individuals or duos to sign up at the door attempt to pun-up each other's spontaneously produced word-play. Winners are determined by the "Human Clap-O-Meter" and go home with a "Mystery Box" prize.
Neon Indian East River Park Amphitheater; 7pm; free
Texas expat Alan Palomo broke out as a chillwave artist in 2011, but has since demonstrated staying power that transcends the defunct microgenre’s limitations. At this free show, he’ll play from last year’s, VEGA INTL Night School, which presented newly fluorescent, loose-limbed electrofunk.
Secret Science Club The Bell House; 8pm; free
Head to the Bell House for this monthly brainiac bash featuring lectures, experiments, custom cocktails and cosmic beats.
The Roy Hargrove Dream Team Blue Note; 8pm, 10:30pm; bar $30, table $45
Hargrove has been doing double duty for a while now, spending half his time as a funkster with his slick combo RH Factor and the other half as a soulful neobopper. Expect this run to synthesize these two equally impressive strains. He's joined by here two giants: drummer Jimmy Cobb who is the sole surviving member of the starry Miles Davis group that waxed the indelible 1959 LP Kind of Blue, and pianist George Cables who was schooled on the bandstand by masters such as Dexter Gordon, Joe Henderson and Freddie Hubbard.
Harold Night Upright Citizens Brigade Theatre; 7:30pm, 9:15pm; $5
The Harold is a classic structure pioneered by improv legend Del Close, and this show sees three of the UCBT’s top house teams take turns in proving they have it down to a fine art in a series of fast-paced, 30-minute sets.
Trivia Tuesdays The Sackett; 8pm; free
Don't let the Sackett's stacked drink menu blur your trivia skills, because you'll need to bring your A-game for five rounds of unpredictable trivia. You'll have to keep up with music, visual, mystery rounds and more if you want to win eternal glory (at least, until the next game two weeks later).
My Blind Brother Solar One; 8pm; free
Rooftop Films and LOFT present a new rom-com starring Jenny Slate, Zoe Kazan, Adam Scott and Nick Kroll. Live music and comedy kicks off at 8pm, followed by the film at 9pm and a Q&A with director Sophie Goodhart at 10:30pm.
Bushwick Flea; 10am; free admission
Tired of the tourists snatching the best retro threads at well-known fleas before you even have a chance to dig? Bushwick Flea joined the area’s market scene last year, and a few vendors from the original Brooklyn Flea sell their goods, so sift through their prime loot and avoid the masses. Other sellers run the gamut from Alpha & Omega jewelry to Zingara Vintage. Bonus: live music every Sunday!
“We Play For You, Butch Morris” East River Park Amphitheater; 7pm; free
Nublu Orchestra pays tribute to Lawrence D. "Butch" Morris using his trademark method of conducted improvisation that avant-jazz, free-funk and more beside. Trumpeter Wadada Leo Smith and ensemble DarkMatterHalo open.
Ice Factory Festival 2016 New Ohio Theatre; 7pm; $18
In the helter-skelter of summer theater festivals, the cool, curatorial heads of the Ice Factory always provide a welcome breeze. This year’s lineup of plays and multimedia performances includes work by Charles Mee, Eliza Bent, Hook & Eye Theater and Piehole.
Amateur Night at the Apollo; 7:30pm; $15–$35
It’s an NYC rite of passage to watch hopeful performers rub the Tree of Hope and give their all to make Top Dog status. Whether the acts dazzle the crowd or are literally swept offstage by C.P. Lacey, they’re guaranteed to produce an unforgettable show. This season’s series of dance, music, comedy and performance showdowns builds up to November’s finals, at which one Super Top Dog wins $10,000 and eternal glory. Be good or begone!
United Nude Sale United Nude pop-up; 11am; free to attend
We’re obsessed with these super-structural and gorgeous kicks (and, yes, you can actually walk in them). Seriously, these heels look like they belong in MoMA. The brand recently opened a summer pop-up in Soho, and it is stocked with women’s styles marked up to 70 percent off retail prices. Snag Web Hi kicks for $195 (were $645), Eros heels for $70 (once $225) and Lo Res pumps for $50 (once $200).
Mortified Littlefield; 8pm; $10
Most of us wouldn’t relive our teenage years if you paid us. But at this reading, bold volunteers share their most embarrassing—and hilarious—childhood diary entries.
Barbra Streisand Barclays Center; 8pm; $100–$620
The top-selling female artist in the entertainment world doesn't play concerts frequently, so every appearance is a special occasion. Along with hits spanning back to the 1960s, expect tunes from her newest CD, Encore: Movie Partners Sing Broadway.
BenDeLaCreme’s Inferno A-Go-Go Laurie Beechman Theatre; 7pm; $22, VIP $40
Writer-performer and RuPaul's Drag Race Miss Congeniality winner BenDeLaCreme takes audiences to hell and back in this multimedia riff on Dante's Inferno. Literate, charming and sincere in its silliness, the show is a diverting mix of comedy, song parodies, puppetry and amusing homemade videos.
Justin Willman Carolines on Broadway; 7:30pm; $32.75
Lighthearted magician Justin Willman, who has appeared on The Tonight Show, Chelsea Lately and Ellen, serves up dazzling sleight-of-hand tricks and belly laughs in equal measure. He hits Carolines for a four-night stint on his Fake Believe Tour.