The main room at Ryles Jazz Club in Cambridge is long and narrow, with a bar on one side of the room and windows looking out onto a busy street on the other. Each table displays images of famous musicians who played sets at the legendary spot—Pat Metheny, Robben Ford, Grover Washington Jr., Maynard Ferguson—but on this night, a Boston College student was the main attraction.
Mike Mastellone, CSOM ’18, got to live his dream.
“I got to be Sinatra for a night ... I wasn’t a college kid who was doing some singing, I wasn’t a member of a group who was singing. For once in my life, I was the star, and it was surreal.” Mike Mastellone, CSOM '18
“It’s always been a dream of mine to have a solo show with my very own big band,” Mastellone said.
He’s had quite the young musical career, playing gigs up and down the East Coast with his high school a cappella group, The Whiptones, including a chance to sing the national anthem as a group at the Mets’ opening day game. He’s been a part of a PBS Special called Doo Wop Generations, where he sang the ’50s pop hits of Bobby Rydell on national television. He’s also enjoyed tremendous success singing with The Heightsmen and the BC bOp! Jazz Ensemble during his time at BC.
He’s had quite the journey through music, but after the television special, he only had one challenge he wanted to conquer before leaving the comfy confines of BC for good.
“I’d never done an entirely solo show,” Mastellone said. “I’ve had solos at other people’s shows, and I’ve had solos at my group’s shows, and I’ve had solos with my high school groups, but it’s never been The Mike Mastellone Show, and I’ve always wanted to know that I could do that. That I could put asses in seats and bring people to see me and fill up a venue and have a show and sing three hours by myself.”
At Ryles, Mastellone sang three hours of Frank Sinatra—one of the artists from whom Mastellone’s nickname “Frankie” derives—and he sold out the old venue. His voice carried throughout the club, soaring through classics like “Luck be a Lady,” as well as arrangements popularized by artists like Dean Martin, Tony Bennett, and Michael Bublé. After the second set came to an end, the crowd rose to its feet to show its appreciation for Mastellone and the Compaq Big Band.
“I got to be Sinatra for a night,” Mastellone said. “I wasn’t a college kid who was doing some singing, I wasn’t a member of a group who was singing. For once in my life, I was the star, and it was surreal.”
“It made me know that not only that I could do this, but that I want to do this. For life.”
But music doesn’t define his entire existence.
Music is just one of the things he loves the most, and Mastellone doesn’t do anything he isn’t passionate about. He makes sure to consider every aspect of his musical life—his motivations, inspirations, and methods as carefully as he can. When Mastellone begins to talk about investment banking, an audience might initially believe his passion for art may not equal his passion for Wall Street.
That audience would quickly be proven wrong.
“From day one at Boston College, I’ve loved music, but I’ve taken my grades very seriously, and I’ve worked very hard to attain the grades and internships that I’ve had, and make no mistake—when I get to New York, my business is going to be first and foremost, my career will be my utmost goal,” Mastellone said. “But if I can keep singing and keep my passion alive while I do the absolute best I can in my career, then that would be something that would make me incredibly happy.”
He credits the balancing act he’s learned as a CSOM student and a performer as the reason he’s ready to balance life as an investment banker with life as an occasional performer.
“People tell me, ‘You’re going into banking? You’re not going to get any sleep,’” Mastellone said. “I already don’t sleep! … I love it! I love being busy, I’m the type of guy—I’m neurotic. I can’t be bored. I can’t go to the beach—it just bores me.”
He’s interned at two investment banks, including Marlin and Associates, during his time in CSOM, and it didn’t take long for Mastellone to realize investment banking was his path.
David Goebel, BC ’16, the former music director of The Heightsmen and Mastellone’s mentor, pushed him in the direction of investment banking early on in Mastellone’s CSOM career.
“It fits my personality as a performer,” he said. “People think, ‘You’re a singer and a banker? How does that work?’ But they’re both just high energy things. When I’m performing, I’m just bouncing off the walls on the stage having a good time. I feel like banking is the same thing: I’m good with numbers, I really enjoy it, I love dealing with people, and that’s the kind of industry where I think I can use my social skills and the analytical skill set I’ve developed here at BC to succeed.”
So in a sense, Mastellone’s musical career has been building to this point—where he’s ended up linking the way he approaches music to the way he approaches investment banking—since high school. He got his start with The Whiptones, an a cappella quartet specializing in oldies. Mastellone’s father introduced him to the oldies when he was a kid, and the younger Mastellone instantly fell in love with everything to do with the genre.
The Ryles show is the ultimate showcase for that. Figures like Sinatra and Martin are artists Mastellone has tried to master for years. While with The Whiptones, he—and the group—concentrated more on doo-wop than the jazz Mastellone often works with now.
“I grew up with Elvis, Roy Orbison, Jackie Wilson, all the greats, Frankie Valli,” he said.
Next came BC, where his music sense seriously expanded. He joined The Heightsmen and bOp! his freshman year. The Heightsmen, which Mastellone refers to as “BC’s only and by default best male a cappella group,” were attractive to him. The all-guys sound has an old-school nature that appealed to Mastellone’s own old-school appreciation.
Mastellone’s time with the group has spanned seven generations of Heightsmen—starting in his freshman year with the three classes above him all the way through the freshmen he mentors now from his post as a senior. He points to the group’s performance of Queen’s “Bohemian Rhapsody” as his favorite Heightsmen-related memory.
“Every single day that we have a practice is just the new best day ever,” Mastellone said.
His nickname, Frankie, comes from two of his music idols: Frankie Valli and Frank Sinatra. As he’s gotten older, the nickname has begun to turn to Frank as he has become one of the elder statesmen of The Heightsmen.
“It’s been an honor working with this musical genius during our time with The Heightsmen,” Pat Fei, fellow senior member of the group and MCAS ’18, wrote in an email. “I know I can always count on him to whip up the most impressive song arrangements, effortlessly and can get a group of 15 guys to sound the best you’ve ever heard. I will truly miss working with him and wish him the best for his future endeavors.”
Mastellone cites bOp! as the place he fell in love with jazz.
“That totally changed my life,” he said. “If Heightsmen is about the brotherhood and the best time of my life, bOp! is about the highest caliber that I’ve been able to achieve for my own self.”
Although ’50s and oldies music is Mastellone’s wheelhouse, bOp! added swing to his arsenal. That’s how he started singing Sinatra, Bublé, and Bobby Darin. He credits Karen Sayward, vocal director for bOp!, as being a primary reason why he’s been able to reach the level of musician and singer he is in 2018.
“From his freshman year evolving as a vocal jazz musician to his last soulful performance of ‘Can’t Take My Eyes Off Of You’ at the recent Arts Festival, Mike has engaged his audiences like a pro with consummate musical expression and energy,” Sayward said in an email. “Additionally, he is an ‘old soul’ with a depth of understanding and appreciation for music of earlier eras. I was particularly enlightened when Mike would enter the rehearsal room chiming out random 70’s pop tunes to which I’d find myself harmonizing or finishing the lyrics he started, and will always cherish these simple, nevertheless joyful daily interactions! We are grateful for his enormous musical contributions to the ensemble, while setting his own high personal standards as a jazz artist and encouraging others to do the same.”
“It’s been an honor working with this musical genius during our time with The Heightsmen. I know I can always count on him to whip up the most impressive song arrangements, effortlessly and can get a group of 15 guys to sound the best you’ve ever heard. I will truly miss working with him and wish him the best for his future endeavors.” Pat Fei, MCAS ’18
Mastellone believes he flat out sounds better in the genre he only started really diving into after he came to BC—that’s what landed him at Ryles on April 5. In a way, that discovery frames his entire perspective on music and life.
“Being a good singer—and I’m not saying I’m a good singer—being a good singer is not about having a great voice,” he said. “It’s about knowing what to do in the setting and how to perform. It’s about song choice. I know people who are amazing singers, and I’ve seen them perform subpar just because the sound choice was off and the performance wasn’t there.”
Trial and error was the only way Mastellone was able to come to this conclusion, which could be painstaking. He’s never had private lessons, he’s had plenty of performances he isn’t satisfied with, but now he knows for sure what his strengths are. He can always go back to songs he thinks are his best: “Mack the Knife” by Darin, “Luck be a Lady” from Guys and Dolls, “I Left My Heart in San Francisco” by Bennett, “Can’t Take My Eyes Off of You” by Valli, among others.
“I Left My Heart in San Francisco” is the piece that stands out to Mastellone from the Ryles gig.
“When you do a ballad, 90 percent of the time it bombs, but when you get a ballad right, it’s beautiful,” he said. “I think for the first time, I’m getting to the point where I’m mature enough in my sound where I can do that kind of stuff. In previous years, even very recently, I was more show than talent. I think I’m starting to get to the point where I’m still a showman and I have my fun but I think I’m starting to understand my voice where I can really make a beautiful song like ‘San Francisco’ beautiful.”
Ultimately, the thing Mastellone is most proud of, though, is the future of The Heightsmen.
“You worry, how is the next generation going to do?” he said. “When we leave, are they going to keep on the legacy? … I couldn’t be more proud and I couldn’t be more confident that not only will they be as good next year—in fact they won’t be as good, they’ll be better.”
Near the end of the second set at Ryles, Mastellone brought up Mike Lyons, MCAS ’21. He said that the passion he saw in Lyons as he sang—the passion in Lyons’s eyes—made him more confident than anything.
Mastellone has some gigs lined up after graduation around the New York area and plans to sing once or twice a month professionally once he gets started in the real world at Broadhaven Capital, a fintech and financial services firm.
“But if I can keep singing and keep my passion alive while I do the absolute best I can in my career, then that would be something that would make me incredibly happy.” Mike Mastellone, CSOM '18
“I still keep in contact with people like Goebel … and I see that they’re still involved in music and they’re still performing once in a while, and it gives me hope too,” he said. “Because I don’t want to lose it. I love investment banking, I’m incredibly excited, and I couldn’t be happier to join this company, but I’m a little afraid that I’m going to lose my music.”
“But as long as I can keep that, I’ll be happy.”
Photo Courtesy of Mike Mastellone