Great Gentlemen of Song with Tony Starlight & John Gilmore

In this special show, Portland vocalist and pianist John Gilmore joins Tony Starlight as they interpret the greatest hits of The Great Gentlemen of Song. Frank Sinatra, Nat “King” Cole, Dean Martin, Louis Armstrong, Matt Monro, Tony Bennett, Bing Crosby, Elvis Presley, Neil Diamond, Elton John, Tom Jones, The Everly Brothers and more. Tony and John pick their favorites and as usual, they open up the second set to your requests!


This show is made all the more special because of John Gilmore’s connection to the Great Gentlemen of Song. John’s dad, Voyle Gilmore, was Frank Sinatra’s record producer at Capitol Records from 1953 to 1958. Drawing on his many conversations with his dad, John peppers the show with one-of-a-kind anecdotes about Sinatra himself and of the legendary recording sessions of which his father was such an integral part. John also has stories about Nat Cole, Matt Monro many more of the legendary artists that worked for Capitol Records or whom he met while growing up in Hollywood. As first prize-winner of the prestigious “Frank Sinatra Awards” during his years at UCLA, John offers his accounts from an insider’s point of view.

Tony and John have a nice rapport on stage and their interchange promises to make this a very entertaining evening.

Tony Starlight: vocals and guitar
John Gilmore: piano and vocals
Dennis Caiazza: bass
Toby Reutter-Harrah: Drums
David Evans: saxophone

Sean Chiles: Lighting director
Aaron Barryman: Sound & Video


Tickets to all shows sold in advance. Walk-ups day of show may be available. Call (503) 517-8584 for tickets after 4 pm on day of show.

Premier Dinner & Show $70 (private table closer to stage)
Standard Dinner & Show $60
General Admission Reserved $25 (Bar stool seating closer to stage, small plate menu available, $10 minimum)
General Admission Show Only $25 (Bar stool & bench seating, small plate menu available, $10 minimum)

Ticketing Fees: $5 per ticket for Premier and Standard Dinner & Show; $3.50 per ticket for General Admission.

For parties of eight or more, please call (503) 517-8584 to make your reservation. There is a 5% discount for parties of 8 or more. There is a 10% discount for parties of 16 or more. Subject to availability.

Clicking “Purchase Tickets” directs you to the Arts People website, where you’ll select seats, choose entrees, and pay by credit card.


Entree choices for this performance

You will be asked to make your selection upon purchase.

A) Chimichurri Bavette Steak: Grilled bavette steak topped with a dill and caper chimichurri.

B) Caribbean Jerk Chicken: Organic chicken hindquarters marinated in Caribbean spices and grilled.

C) Braised Coconut Spinach with Black Beans (vegan, gluten-free): Spinach braised with coconut milk, lemon, ginger and sundried tomatoes. Served with black beans.

All entrees served with seasonal vegetables and cilantro basmati rice, bread, house salad, and dessert.

Arrival Timelines & Service Fees for Gentlemen of Song

Premier and Standard Dinner & Show Packages
Seating begins no earlier than 6 PM
Dinner Service begins approx. 6:45 PM
Please call if delayed after 6:45 PM
Show begins at 8:00 PM

There will be a $4 service charge per guest added to your bar tab at the show — this is a baseline gratuity for your dinner service. Please tip appropriately for beverage service.

General Admission Show Only Seating
Seating begins no earlier than 7 PM
Arrive any time between 7:00 – 8:00 PM

Enjoy beverages from our wine and cocktail menus, and small plate menu.
There will be a $10 food/beverage minimum at the show. Please tip appropriately for food/beverage service.

Corkage Fees

$15 per 750 mL
$30 per Magnum (1,500 mL)


Keep up to date on all the shows, special events and fantastic happenings with Tony Starlight and at The Tony Starlight Showroom.

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Tony Starlight Showroom
1125 SE Madison St
Suite 103G
Portland, OR 97214
(503) 517-8584

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