Cabaret Roundup: Oct. 5-11 – Deborah Cox, Maltby & Shire & More in NYC

Are you trying to plan your entertainment for the week or looking for a fun show to see this weekend? We have you covered with jazz, cabaret, comedy, and more! NYC has so many incredible events, but here are a few top picks to consider this week including the New York Pops annual benefit featuring Deborah Cox, a Jerry Herman tribute, and more.

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NEW YORK POPS UNDERGROUND CABARET at 54 Below
Mon. October 5 @ 6:30 pm

Tickets available here.

Guests will enjoy a special cabaret performance from Grammy and Tony-nominated singer and actress Deborah Cox. Alumni from The New York Pops’s Kids on Stage program will serve as opening act. During the performance, guests will enjoy a meal with wine pairings. All proceeds from The New York Pops Underground support our PopsEd music education programs, which provides life-changing music education experiences to New York City students.

Tickets: Tickets start at $365.

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American Songbook Association Sixth Annual Gala - Maltby & Shire: Our Story Goes On at Kaufman Music Center
Mon. October 5 @ 7:30 pm

Tickets available here.

Cabaret Scenes and the American Songbook Association (ASA) announces its sixth annual gala Maltby & Shire: Our Story Goes On honoring the multi-award-winning songwriting team of Richard Maltby. Jr. and David Shire. Celebrating the team behind the musicals Baby; Big; Starting Here, Starting Now; Closer Than Ever; About Time, and beyond, the evening will feature special guest performances by Loni Ackerman, Liz Callaway, Margery Cohen, Jenn Colella, Judy Collins, Catherine Cox, Gretchen Cryer, Beth Fowler, Judy Kaye, Eddie Korbich, Charlotte Maltby, Sally Mayes, Ethan Paulini, with others to be announced. Deniz Cordell will serve as musical director.

Tickets: Tickets start at $75.

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Ali Ewoldt: When You Wish Upon a Star, feat. Jose Llana & more! at 54 Below

October 6 @ 7 pm

Tickets available here.

A dream came true for Ali Ewoldt when she became the first Asian-American to star on Broadway as Christine Daaé in Sir Andrew Lloyd Webber’s The Phantom of the Opera. It was one  of many such dreams that have come true for this Broadway star, including landing major Broadway roles in Les Misérables and The King and I. On October 6th on the 54 Below stage, Ali Ewoldt will share those dreams with you, singing the famous songs she performed on Broadway, as well as the equally famous songs she performed on her journey to the Great White Way: Disney hits, musical theater classics, and more. This will be a show bursting with Broadway hits by an actress who has walked the walk and sung the songs!

Tickets: Tickets start at $25. There is a $25 Food & Beverage Minimum

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Judith Owen at Café Carlyle

Oct. 6-7 @ 8:45 pm

Tickets available here.

Genre-defying singer, songwriter, and storyteller Judith Owen makes her highly anticipated Café Carlyle debut with a special two-night engagement on October 6 & 7, 2026. Known for her wildly charismatic live performances - part concert, part theatre - Owen seamlessly moves between jazz, blues, big band, rock and musical theatre, creating “mini-musicals” filled with humor, heart, and fearless musicianship.

Tickets: General Seating $142  per person / Premium Seating $197. For general and premium seating, there is a food minimum of $95 for two courses. Bar seating is sold out.

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Brian Newman at Café Carlyle

Oct. 8-9 @ 8:45 pm

Tickets available here.

Café Carlyle is delighted to welcome legendary performer Brian Newman back to the stage for two-nights on Thursday, October 8 and Friday, October 9, 2026. Hailed as a true Tastemaker and a Creative and Musical Director of exceptional caliber, Newman is a Grammy Award-winning producer, acclaimed bandleader, trumpeter, and vocalist whose Signature Sound and artistic vision have left an indelible mark on New York City’s vibrant music scene. With over 25 years of experience curating and crafting unforgettable live performances across premier venues—ranging from nightclubs and luxury hotels to cinematic and television productions—Newman is a consummate showman whose artistry bridges generations. His deep reverence for jazz legends like Miles Davis and Chet Baker, combined with a passion for the Great American Songbook, is infused with modern flair through influences including Nirvana, Willie Nelson, Earth, Wind & Fire, Thin Lizzy, Bruce Springsteen, The Police, and more. Most recently, Newman and his band collaborated with Lady Gaga on the orchestration and recording of her album Harlequin and delivered a standout appearance on Jimmy Kimmel Live! The group also contributed to the soundtrack of the highly anticipated film Joker: Folie à Deux.

Tickets: Tickets start at $104 for bar seating. For general and premium seating, there is a food minimum of $95 for two courses. Bar seating has a $60 food/drink minimum.

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HELLO, MACON! A Musical Tribute to Jerry Herman at 54 Below

October 10 @ 9:30 pm

Tickets available here.

Fresh off the success of his debut cabaret run MACON: His Own Way!, 2026 MAC Award Nominee (New York Debut – Male) Macon Prickett returns to Broadway’s Living Room with HELLO, MACON! A Musical Tribute to Jerry Herman! Join the “boisterous boy with the big voice” (BroadwayWorld) and his band, led by the incomparable Canaan J. Harris, as he pays homage to the Tony® and Grammy winning show-business legend! Expect to hear arrangements of classic Herman hits from Mame, Hello, Dolly!, La Cage aux Folles, Mack and Mabel, The Grand Tour, and more! This is Macon’s love letter to the man whose music made him fall deeply in love with musical theatre and the dames who brought his songs to life!

Tickets: Tickets start at $19.50. There is a $25 Food & Beverage Minimum