'I Can Sing That.' 'Strange Loop' Alum James Jackson, Jr. Connects with Favorite Songs for Ptown Cabaret

When James Jackson, Jr. headed to New York after college for auditions to Broadway shows, he heard a familiar meme. "I didn't know how to audition," he explained this past August via phone. "So I would go in and sing something like 'Bring Him Home' from 'Les Miz.' And I was immediately told, 'Oh, you can't sing that.'"

This sort of reaction was nothing new for Jackson. "When I was at college and studying opera – I talk about this in my show – I wanted to sing 'Dalla sua pace' from 'Don Giovanni.' This gorgeous tenor aria I worked so hard on. And I was told, 'You don't need to learn that because you're not going to singing in Don Giovanni.'"

Or he was addressed in coded messages. "I was asked by someone at an audition, 'Do you have anything more urban?' And someone else asked, 'I like what you did, but can sing more like Billy Porter?'"

It was, coincidently, the same response that his friend and collaborator Michael R. Jackson (no relation) was hearing when he was pitching his musical "A Strange Loop" during its long 15-year journey to its first professional production. "I remember no one thought Michael's songs could play on Broadway," James said in an interview earlier this summer. "They're too gay. They're too Black. They're too all of that."

But the songs connected with James, who joined Michael on his journey and stayed with the show for 13 and a half years, if only because the show spoke so personally to the experience of being a Black, queer man in America. "It spoke to a lot of things at the core of just who I am as a person, who Michael is as a person. But we also found a commonality and a friendship."

"A Strange Loop" follows the inner turmoil of an aspiring musical theater writer who supports himself ushering at Broadway's "The Lion King." Usher, as he calls himself, wants to focus on putting onto the stage what it is like to "travel the world in a fat, Black, queer body," but his Thoughts (played by six actors) continuously sabotage him. James played the most self-destructive of all: Self-loathing. "I played a bitch in the show," he recalled. "I was the deal. I was self loathing, so I was not nice to people. So James made it a point to, I have to go out front after every show to meet people. I had to let them know that I'm not a bitch. I just play one on stage, I swear to God."

Asked what he will be performing this Friday and Saturday at Provincetown's Post Office Cafe and Cabaret, James says, "Material-wise, it is more of a traditional cabaret. There will be a few songs I did in my Juneteenth show, Ray Charles' 'Hallelujah I Love Her So' being one of them. The highlight for me this go around is that I'm bringing my trusted piano player and music director, Elliot Roth, who I've worked with for the past 13 years. He'll also be handling arrangements for the album we are working on later this year."

"Even before 'A Strange Loop,' I have connecting to the music that I have always been told I cannot sing. I'm not supposed to do that. And much of this music was the music I grew up with. My mother had great taste in music. So, I can go from a Nina Simone song into a Tori Amos song, I sing opera in my shows. I sing what speaks to me, and people afterwards are surprised, like, 'Oh, I've never heard Pat Benatar song like that.' Or, 'I didn't know that you can connect Pat Benatar and Ray Charles.' Like, yeah, you can."

So don't be surprised to hear songs by Tori Amos, Nina Simone, Pat Benatar, Ray Charles, and Stephen Sondheim. They also are his reaction to being told he couldn't sing some songs. "My song choices speaks a lot to me having been told you can't do something. It's just not me being bratty and saying, 'Well, I'll show you.' Instead, it is me just saying, 'I can. Just listen.' And folks seem to be impressed or moved by it, and I think it's a really beautiful exchange."

For the longest time, James steered clear of Broadway material in his cabaret act. "I was terrified to go into that world," James confides. But during "A Strange Loop," that evolved – including one Sondheim song he was told he "was not to sing": "A Glamorous Life" from "A Little Night Music." Not the stage version; the one written for the ill-fated musical version in 1978 that has been made famous by Audra McDonald in concerts. "It is my favorite Stephen Sondheim song – the most beautiful song he has ever written." In the song, a teenage girl sings of her mother's far-less-than-glamorous life as a stage actress. James said he thought of the song a few summers before while teaching young theater students in Provincetown about Tennessee Williams. "And I found these Tennessee Williams quotes and interviews and things about him and his own mother's relationship. And I thought of this song, and I figured out how to do it. The response has been great across the board. I had one gay man say to me, 'I am going to hell for saying this, but I never want to hear Audra sing it again.' I don't think they've ever heard the song sung from the point of view of a man."