After doing more than 150 Random Roles for The A.V. Club, it would be nearly impossible for me to look back at the interviews I’ve conducted for the feature and narrow it down to my single favorite conversation. I can, however, tell you—and without so much as a moment’s hesitation—the most profound relationship I’ve ever had with someone I’ve interviewed for Random Roles.

It’s almost become a running joke about how, whenever I talk to someone for the feature and they say, “I should write a book,” I reply by saying something like, “Well, if you need a co-writer, you know where to find me.” But only one person to date has ever contacted me afterwards and said, “You know, I’ve been thinking about the book. Are you still interested?”

Although he posed this question in an email, I swear to you, I could hear his voice in my head just as clear as day, and I’m guessing there’s a pretty good chance that you heard it when you were reading it, too. That’s the kind of voice Alex Rocco had: instantly memorable and completely unforgettable. As I soon discovered, that’s exactly the kind of guy he was, too.

From the very beginning, there was something a little bit different about my interactions with Rocco compared to my previous Random Roles interviews, starting with the fact that he made a point of reaching out immediately after the interview went live. It was just a brief message, but he took the time to praise the piece, praise me as a writer, and offer his thanks, reiterating his email address (“if you want to keep in touch”) and closing by thanking me again and saying, “It was fun talking to you!” I wrote him back, of course, telling him that I was glad he’d enjoyed the piece as much as I had and—remembering that we’d had to split our interview into two calls because I’d had to take my daughter to her ballet class—I attached a picture of my daughter in the outfit she’d worn for her butterfly-themed birthday party, so that he’d have a frame of reference to the kid that had me so wrapped around her little finger that I had to ask Moe Greene if I could call him back. When he wrote me back a little over two months later with his question about the book, he added, “Hope the ballet butterfly beauty is still dancing.”

After another email and a few phone calls, it was decided that I’d have a proper sit-down with Rocco when I came to Los Angeles for the Television Critics Association press tour. The specifics of the meet-up were very much scheduled on the fly, to the point where we only confirmed the date of our meeting a few hours before it actually took place. Being a stranger in a strange land without a rental car, I took a cab from my hotel to Rocco’s residence, where I was greeted warmly by his wife, Shannon. She and I chatted for a few minutes in their living room while we waited for the man himself to emerge (during which time I couldn’t help but giddily notice his Emmy for The Famous Teddy Z sitting on a nearby shelf), and during the chat, what I experienced was, for lack of a better phrase, the sweetest possible grilling a guy could get. But it made perfect sense: wouldn’t you want to know as much as possible about the person who might be helping your significant other write his memoir?

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When Rocco came out, he immediately enveloped me in a hug, wanting to make sure that Shannon had been taking care of me, asking about my family and demanding to know every little detail of my time in California thus far. After an appropriate amount of chit-chat, we got down to the business at hand. The conversation was all very casual. Serious, yes, but it was still just a couple of folks chatting… or, more specifically, he was talking, and I was soaking it all in. He told me what he’d been thinking about for the book, what parts of his life and times he wanted to discuss, what skeletons he was toying with unearthing, and this, that, and the other. He and Shannon spoke openly, I listened intently, and then we had a back-and-forth about what they envisioned and what I envisioned. When we wrapped up, they refused to let me take a cab back to the hotel, so after taking a picture with Rocco, who made sure that I had a signed photo of him from The Godfather to take home, Shannon drove me back to my temporary place of residence. The whole experience was surreal, but wonderfully so, and no matter what might happen from there, I knew I’d still have a souvenir from the experience that I’d treasure forever.

A month or so passed after that in-person encounter, and I tried not to be overanxious about the fact that I hadn’t heard anything, but when Rocco turned up on an episode of Private Practice, I used it as an excuse to send him a text and congratulate him his performance. He wrote me back to thank me, but that was the extent of the conversation, and while I had no reason to believe that I’d said or done anything during my visit to turn him off of the idea of collaborating with me, the silence—which continued for another two months—was killing me. Finally, Rocco decided in early 2013 that, yes, he wanted to at least start taking some baby steps with the book, if only to see how well the two of us could work together.

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Rocco and I talked probably a dozen times, each occasion lasting for at least half an hour, and the conversations were goddamned glorious. He’d check in by text to see if it was a good time to hop on the phone, and he always asked how my wife and daughter were doing. In fact, when we first started having the conversations for the book, he had a nice, long chat with my wife, during which I am assured that he had nothing but the highest praise for me, and he even promised to make her an authentic Italian dinner the next time she accompanied me to Los Angeles. At one point, Rocco texted me just as my daughter had gone out to play in the snow, so I sent him a picture of her in the front yard, and he wrote back, “I wish I was there throwing snowballs with her!” Later, my wife would reflect in awe on how easily he ingratiated himself into our lives: in the blink of an eye, it had somehow become the norm for her to answer the phone and hear that familiar raspy voice say, “Hi, Jenn, it’s Rocco. Is Will around?”

When we talked, Rocco regaled me with stories that he envisioned being in the book as well as stories that he didn’t want in the book but that he just wanted to tell me. At one point during this period, he auditioned for a small role on a prime-time sitcom, and he asked me what I knew about the show and if I thought it was funny. As you might imagine with that glorious voice, everything he had to say seemed worth hearing, and every story seemed absolutely amazing at the time he was telling it. Better yet, when the time came to sit down and transcribe them, most of them played out just as well on the page.

You’ve probably deduced by this point that the book did not come to pass, which—if I’m to be perfectly honest—remains one of the biggest disappointments of my life, but I can take comfort in the knowledge that it wasn’t because Rocco and I didn’t work well together. Ultimately, things began to fall apart because I took one of his stories and made it play a little too well on the page.

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I can’t speak to what the story was about—I’m going to maintain the same discretion now that I’ve maintained all along—but I can comfortably say this much: It was a story that he’d cited from the very beginning as something he’d wanted to discuss, something he was confident would be a selling point for any resulting book, and when I sent him the piece that I’d built from his words, trying to do my best to capture his voice, he admitted amazement at how quickly I’d constructed it and confirmed that it detailed things exactly as they’d happened. The problem, ultimately, was that it was so effective in capturing the moment that it caused him to second-guess his original plan for the direction of the book. He’d shifted away from his earlier interest in telling stories about his days in Hollywood and was more interested in discussing his sordid past, following the path that led him into jail all to the way to the end, when he eventually found his way out of a life of crime and into a career as an actor. And yet even as he was changing direction, he was still praising my efforts, thanking me, and saying, “This is going to be fun. I really look forward to working though this and discovering where it will naturally lead us.”

So we continued to talk on the phone. Rocco told me stories about his youthful indiscretions in Boston, and I dutifully listened. When he said that he wanted to take things in a darker direction, focusing on the grittier side of his life and discussing his proximity to Whitey Bulger and the Winter Hill Gang, I was fine with that. But because I simply couldn’t imagine the book without all of his great stories about his experiences in Hollywood, I’d still ask him about some actor or director he’d worked with, confident that there’d be a good story there, and I was never left disappointed… until the day he called and informed me that he’d decided that he wanted to stop work on our project and part ways, “no hard feelings.”

It was so unexpected that I found myself stammering and all but crying out, “I don’t know what I did wrong, but I can change!” But he didn’t want to fix anything, and he didn’t even really want to try to explain why things weren’t working out. He just wanted to break up. And having done so, he asked me to give his love to my wife and daughter, and then he said goodbye.

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Rocco was certainly well within his rights to step away and call it quits: We’d signed no contract, and it was established up front that we were simply feeling each other out as collaborators. He’d seemed so happy with my efforts as a writer, though, that I just couldn’t comprehend why this had happened so abruptly. I sent Shannon an email a few days later, asking if she could shed some light on exactly what had happened, which she did to the best of her ability, but the long and the short of it is that the story that I was most skilled at telling was no longer the story that he was most interested in telling. And that’s fair enough. But it still broke my heart, and since I knew I wasn’t going to be able to change his mind, I just didn’t have anything else to say to him.

The better part of a year and a half passed before I broke the silence between Rocco and myself, when I decided to text him my condolences after the death of someone I knew he’d been close to, and he responded with thanks and, as ever, a request to “give my love to your family.” A few months later, when I embarked upon—of all things—an epic oral history of The Facts Of Life, I dropped him a line to see if he’d be up for contributing. Instead of writing me back, he just called me, and suddenly it was like old times. He gave everything for the piece that I’d hoped to get from him, and then—after he asked me if I’d talked to his TV daughter, Nancy McKeon, and I told him I was still waiting to hear back from her publicist but had my fingers crossed—he promptly (and absolutely without any suggestion from me) contacted her and said, “C’mon, you need to talk to this guy, he’s good people.” So she did. And I must’ve lived up to her expectations, because after we talked, she dropped me an email and said, “Rocco was right.”

The last time I had any communication with Rocco was immediately after the Facts Of Life oral history debuted. After he read it, he sent me a message saying, “Great stuff. Loved it. You’re very talented. Love to your family.” I wrote back, thanking him, telling him to give my love to Shannon, and—just because it felt right—I added, “You know, my wife said that she’s still holding you to that home-cooked Italian dinner you promised her the next time she’s in L.A.” His response: “Done deal,” followed by a smiley face.

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That the deal will never be done is undeniably sad, but the fact that the last thing Alex Rocco ever sent me was a smiley face is actually kind of awesome. In fact, as I reflect on it at this very moment, I can hear his voice in my head saying, “Aw, that’s great!”

As for my conversations with Rocco, I know that the flip side of not having a contract is that I can ostensibly do whatever I want with them, but at the moment, I don’t really want to do anything with them, and I’m not sure I ever will. If I do, it almost certainly won’t be without getting in touch with Shannon and seeing if there’s any way I can do something with her blessing that would honor Rocco’s memory, but it’s far too soon to be contemplating anything of the sort. But no matter what I end up doing, even if I end up doing nothing at all, I can still take comfort in something my cohort Nathan Rabin told me when I first began the up-and-down ride with Rocco: “If nothing else, you’ll have a whole lot of amazing stories to tell your kid.”

Boy, do I.

Of course, because of the language, I probably won’t tell her most of them till she’s 18. But you’d better believe they’re worth the wait.

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