PLAYBILL PLAYLIST: Sierra Boggess, Jackie Hoffman and More Pick Favorite Judy Garland Performances

The fourth annual Night of a Thousand Judys will take place June 16 at Merkin Concert Hall. In anticipation of the concert, concert cast members Sierra Boggess, Jackie Hoffman and more pick their favorite Judy Garland performances as part of this week's Playbill Playlist.

Presented as part of Justin Sayre's series The Meeting*, the annual event serves as a benefit for the Ali Forney Center and its mission to assist LGBT homeless youth.

Jason Wise will direct and choreograph the evening that will "honor the iconic Judy Garland with special skits, tributes and songs from her legendary career as movie star, recording artist and stage performer." Expect a special tribute to "The Wizard of Oz" as well.

The 8 PM concert will feature Randy Harrison ("Queer as Folk"), Bridget Barkan ("The Tonight Show"), Joseph Keckler, Natalie Douglas, Sierra Boggess ( The Phantom of the Opera), Austin Scarlett (“Project Runway”), 60s pop singer Karen Wyman, two-time Tony Award nominee Alison Fraser, Jackie Hoffman ( Hairspray), jazz violinist Aaron Weinstein, Grammy Award winner Jane Monheit, Tony nominee Rory O'Malley ( Book of Mormon), Julia Murney ( Wicked), R&B singer Sarah Dash, folk-rock performer Erin McKeown and Gabrielle Stravelli.

In anticipation of the evening, host Sayre and cast members Boggess, Hoffman and Harrison pick their favorite Garland performances and tell us why they made the list. 

For more information, visit AliForneyCenter.org/Judys.

Sierra Boggess: "Have Yourself a Merry Little Christmas." Has anyone ever sung it better? I LOVE everything she sings in "Meet Me in St Louis," but this one always stuck out for me. The tones in her voice are so haunting and beautiful as she sings probably the saddest Christmas song ever!

Sierra Boggess: "Get Happy"/"Happy Days Are Here Again." Now, of course I love that she sings this duet with Streisand. I mean, it's just a slice of HEAVEN, but I LOVE the way she clutches Barbra so sweetly as they sit on those stools together!! And, I love, love, love the words of "Get Happy" and how they arranged this duet so that what usually is an up-tempo becomes very legato and forces you to really listen!! And, GET HAPPY!

Sierra Boggess: "I Don't Care." I'm absolutely obsessed with this song and how she sings and performs it. How she came up with those moves for the chorus I will never know, and it's genius. And then getting down on one knee basically doing the cover of "Star is Born" as her final pose! Oh, I can't get enough!!

Sierra Boggess: "The Man that Got Away." The vocal and emotional intelligence she displays in this song is so inspiring. You feel every note and word along with her. And the movie version, when she's surrounded by the band and just using her voice as a total instrument along with them…! You can tell they just let the camera roll, and she organically did what she felt in her soul!

Randy Harrison: "Come Rain or Come Shine." I love this song, and my favorite version is when she performed it on Ed Sullivan in 1965. This arrangement makes me think I'm going crazy in a good way. Those bongo drums at the beginning give my heart palpitations, and then you hear the piano pounding her opening pitch, and it sounds like "Jingle bells, jingle bells!" Her expression is really hard to read at the beginning. I can't figure out what she is thinking, or if she wants to be there. It's like: She's gonna love you like nobody's loved you, but does she really want to? This ambivalence adds tons of weird complexity to a lyric that is so un-ambivalent. Then she gets this kind of teasing wink in her eye. Near the end when she says, "Won't that be fine," I can't help wondering if she's being sarcastic, especially knowing what a wicked sense of humor she had. It's from that moment on she taps into this primal kind of anger and seems to be having the time of her life. Maybe I'm reading too much into it. It's a brilliant performance. I just watched it seven times.

Randy Harrison: "What Now My Love?" This is originally a French song called "Et Maintenant." I guess the fact that it's French and it has that military kind of drumming, it brings to mind "Je Ne Regrette Rien." You could totally imagine Piaf singing this song, which is cool. I think there are some fascinating parallels between Piaf and Garland, both musically and biographically. I wonder if anyone's ever written a thesis about it. Even though the lyrics are so dreary, those plodding, never-stopping drums sound like marching and, in my mind, work against the lyric and transform the song from a torch song to a song of survival. That, and the last lyric being "good-bye" delivered like a triumphant "f*ck you." There's a great version of her performing it on Perry Como's Kraft Music Hall in 1966. I kinda think the live recording from the Palladium is too slow.

Randy Harrison: "The Party's Over." I love this song. There's a version on YouTube recorded at the Manhattan Centre in 1962. Apparently, she had a sore throat, and she does sound a bit hoarse, but I think it makes the song even more heartbreaking.

Randy Harrison: "The Trolley Song." Doesn't this song make everyone happy? If you don't know this song, how can you possibly understand how to express the feeling of the first time you hold the hand of someone you are falling in love with? There's this goofy version she did on her show where Mel Tormé sings "the man's point of view" of the song, and Judy's last note is prerecorded and extends forever. It's bizarre but hilarious, and they seem to be having a good time.

Randy Harrison: "Paris is a Lonely Town." I'm a fan of all Judy's city songs ("Chicago," "San Francisco," "I Happen to Like New York"), but "Paris is a Lonely Town" takes the cake for me. A torch song that epically reaches the point of suicide. Watching her beg the Seine to be her lover is devastating, and God, does she mean it! I've had some dark days in Paris, so I get it. It can be a bleak lonely place. The performance she did on "The Jack Paar Show" is astounding.

Jackie Hoffman: "The Man that Got Away." I'm sure this is on everyone's list, but I just have to. I am a gay man at heart.

Jackie Hoffman: "Have Yourself a Merry Little Christmas." I get a silent thrill because it's superb and, of course, written by a Jew.

Jackie Hoffman: "Swanee." It doesn't get more old-school than this. An homage to a Jewish performer who imitated black people.

Jackie Hoffman: "Dear Mr. Gable." Such a sweet and innocent Judy. Also, it's unusual to see one star sing about another star.

Justin Sayre: "Every Little Movement." It's one of my favorite moments in all the films of Judy Garland. Judy plays a young girl trying to get her start in the theatre. Her audition goes poorly and alone and, feeling sorry for herself, she meets this cleaning woman. The cleaning woman reveals that she used to be a star, with her own signature song and everything, and gives Judy advice about the tough life on the stage. They sing together the cleaning woman's signature song. I love Judy's generosity, her hope and her kindness as she steps into her own spotlight.

Justin Sayre: "I'm Always Chasing Rainbows." Judy's dad in this movie is an old vaudevillian who knows how to "put over a song." And, when Judy tries to do the same thing, the way Dad taught her, she fails. Dad, sitting at the piano is a little broken, but Judy gets another chance and does the song her way. It's magic. And, in two-and-a-half minutes of film, tells a three-act play.

Justin Sayre: "Happiness Is Just A Thing Called Joe." I love Judy singing all of Harold Arlen, but this is easily my favorite Arlen song. And it's to her son, Joe. It's touching and beautiful.

Justin Sayre: "Old Man River." The greatest moment on television. Ever.