2026 Update: James

0:06Pushkin.

0:10Um, hi. Hello, hi. Back in the studio again. Back in the saddle. Today we're gonna knock on the door of an old friend of yours named James. Ah, okay. This is a first season episode. Yeah, way back. To me, it's one of the funniest episodes. Yeah, it's very funny. And it's also one that I would come back to when I was kind of missing my friends. Oh, that's nice. When I was missing both James and Howard, I would just put on this episode and it felt like I could spend a little bit of time with them. it is funny that at the time when we, you know, went off on our mission for this episode, full of hope and shenanigans in our heart or whatever, we felt like kind of over the hill, you know, we felt like this is like kid stuff, you know, we're like men in our mid 40s, you know, and what are we doing?

1:07But now listening to it from the vantage point 10 years later, I feel like, wow, were we ever so young? Ten years. My goodness. Yeah. A lot transpires, it turns out, in the course of ten years. It certainly does. Yeah. And at the end of the episode, I check back in with James to see what his life has been all these years later. Well, enjoy. Enjoy indeed. Please make sure the volume is set at a temperate number. Oh, but first, a word from our sponsors.

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5:05Horrible timing. Six kids in my house, two parents, and getting kids ready for Halloween. Jonathan Goldstein calling for Dr. Jackie Cohen. I gotta go. Wait, wait, wait. Hello, Jackie? You know what? Okay, you're a doctor, right? Hurry up. I'm starting to realize, like, in the past year, I'm... Hurry! I'm pretty convinced I'm... Hurry! I'm losing hair. You're bald. Balding. Bald. It's a process. So bald. Now, I'm trying to figure out if it's a symptom of something. I gotta go, John. I got to go. The party starts in 15 minutes. You're having a party at your house? Why didn't you invite me over?

5:56Do you want to just do the show? Or...

6:06From Gimlet Media, I'm Jonathan Goldstein, and this is Heavyweight. Today's episode, James.

6:24When he was a kid, James loved taking long walks with his dad, Douglas. Douglas was a film buff, and during these walks, he'd recount the plot to every movie he'd ever seen. Hitchcock, Kubrick, James loved it, and when he grew older and finally got to see the actual movies, as good as they were, they often paled beside the versions his dad told. Something of a dreamer and an eccentric, Douglas lived his life as though he himself were a character in a movie. He died that way, too. On his deathbed, he issued an unexpected final request. The request was that we scatter his ashes on the 18th hole of the golf course he loved.

7:15Each of Douglas' kids was handed a different task regarding the estate. James was put in charge of the ashes. My dad was probably the most important person to me, outside, obviously, of my wife and kids. When he died and when the will was recorded, I wasn't there. You were actually there, I think. I was there. Douglas was nearing the end and urgently needed to sign his will, and James, who lived out of town, couldn't make it in time, so he asked me and our other good friend, Howard, to go to his father's bedside and bear legal witness to the signing of the will. To this day, James still carries around a lot of regret about not being able to be there.

8:02Although I know it's unlikely, My memory of that day is of Douglas wearing an ascot tucked into his hospital robe. Regardless of whether he actually was, Douglas was the kind of man who always gave the impression of wearing an ascot. As always, he was gentlemanly and cordial. This in spite of the fact that he would pass away within the next 48 hours.

8:31Douglas was born an illegitimate child in a poor part of England and raised by a single mom. As a young man, he felt judged and carried with him the feeling of always having to prove himself, even going so far as to affect a posh, upper-class accent. For Douglas, golf was the domain of the wealthy and sophisticated, and having his ashes placed on the 18th hole of his beloved golf course, an event that James says he probably envisioned being accompanied by bagpipes and artillery, would mean finally receiving his due. But James is yet to honor his father's request. It's now been 16 years. Is it just procrastination?

9:12That's what I told myself. Yeah. I can vividly remember, you know, a day afterwards thinking, oh, yeah, the simplest thing. In fact, it seems so simple that we'll get to it. And now, 16 years later, it's very complicated. I think, to be honest with you, there's part of me that wants to hold on to them because it's my dad.

9:43And so the urn moved from mantles to closets. For a long time, it even knocked around in the trunk of James' car. It now sits on a shelf in his basement.

9:56Do you think it would be a load off your head if you were able to spread the ashes? The amount of times I cried, you know, going on about what a terrible son I was, to not honor his request and the guilt I have about the way he died and, you know, I didn't deal with it well, and it's all a piece.

10:24He, as he got sicker and sicker, he wanted to go home desperately, and myself and my siblings decided he could not go home because he was a hoarder. Though it wasn't clear that he ever used them, Douglas had an entire room filled solely with golf clubs. Having lived through the war, he also saved empty TV dinner trays, old microwaves, and broken radios that he'd find on the street. We decided he could not go back there, and he was so upset about that, and he went out just really angry. He just wanted to go home. I can't fix the way he died, but this was his one request, and I haven't honored it.

11:10and not only would I be putting to bed something that's been just dogging me for years, I think I'd also feel pretty proud of myself that I'm the person I want to be. Since the person I want to be is the person who helps people be the people they want to be, I asked James if he'd like me to help him lay his father's ashes to rest. And James said, Yes. Would you want to do that? Yeah, of course I do.

11:41The objective? Infiltrate Douglas' fancy old golf course and scatter the ashes. The obstacles? Septuagenarian narcs with prying eyes, not to mention the fact that scattering earthly remains is against the law. For this to work, we need the right team. James was the key man, our entry point into the operation. And I was the bank, bankrolling the green for expenditures. All that was missing was a front man, We needed a person of quick wit. Look at that, right off the bat. Fat, cat, sat, fat. Someone cool under pressure. What's that on my arm? We needed... Oh, that's arm here. Howard. Not only was Howard our oldest friend, but he was there with me the day the will was signed and the directive was given.

12:30And to top it off, Howard never met a grift, swindle, or flim-flam he didn't think was eggs in the coffee okay. Fill your pockets with extra after-dinner mints at the local diner? Check. Avail yourself of ill-gained coffee refills through a counterfeit Russian senior's card? Double check. Howard was always on the make and up for anything.

12:54The date had been set. Sunday. Which also, as it happens, was Father's Day. The team was in place. We just needed to sort out logistics. Thursday, 8.48 p.m.

13:34one. Some booze maybe might help steal our nerves. So do you want to try to go there and play golf? No, I've never golfed. I don't know how to golf. I've never golfed either and it's the 18th hole too so I wish it was the first hole because we could just go and suck and then do our thing. He specifically needs the 18th hole, right? 18th hole. It's the last hole. But if there's someone there watching us, how do we do it? The clubhouse is near the 18th hole. It looks over the 18th hole, so that's another challenge. What's a clubhouse? Clearly, there was a lot of work to be done.

14:219.32 p.m. A quick look at the golf course website reveals a very specific dress code. Polo shirts, belts, golf shoes, something called a tilly hat. If wearing a polo shirt with some kind of bonnet wasn't embarrassing enough, the rules explicitly stated that all shirts were to be tucked in to your pants. For this to work, we need to honor the dress code to a T. In short, we need the best disguises money could buy. And as the bank, it was my job to secure the greenbacks. After a brief parlay with Gimlet founder and CEO Alex Bloomberg, I'm told my budget is$50. To which I say, but I've already promised the crew I'd take them shopping at JCPenney, and now I'll look like an idiot.

15:07To which he says, what crew? And I say, never mind. Alex then tells me to take it up with Matt, because he's in the middle of a boardroom meeting, but Matt scares me, so I just convert the green to Canadian travelers checks. A safe, responsible move, so Alex, if you're listening, you should at least cover the service fees, except you probably aren't listening because you're too busy with your precious startup.

15:31So, although it probably wasn't the kind of establishment James' posh dad Douglas would approve of, we'd need to hit the only place we could afford. Friday, 12.36 p.m. It turns out the sports section of a goodwill can be a pretty sad place. Unstrung badminton rackets, waterlogged Nerf footballs you only hope are logged with water, and... One boxing glove, that's... As an advanced student of the heist film as genre, I know that when pulling off a big job, the perfect outfit is crucial. Think Michael Caine's luxe white turtleneck in The Italian Job or Elliot Gould's neckerchief in Ocean's Eleven.

16:15They have some very nice slacks here, I will say. And the prices are very affordable. You want to try on the polo shirts? Not exactly Frankie Munez's wraparound shades in Agent Cody Banks, but it'll have to do. Look at these two. Ooh! It's like rayon. What's how soft this is? The good news is that the Goodwill has changing rooms. The bad news is that there's only one, and it's about the size of a bus station toilet stall. I'm going to come in with you. But since we are A, a team, and B, absolutely fearless, together we cram in, and like any team would, strip completely naked. That might be the ugliest shirt I've ever, ever seen.

16:55I kind of like it. It bears mentioning that the shirt Howard is referring to is creamsicle orange and bears the logo of a plumbing company. And, luckiest of lucky days, he's found the exact same shirts for me and James. This way, he reasons, we can all match. Like a crew. It looks good. You're not supposed to look good. It's golfing. Stupid. Oh, man. Howard, James, and I have known each other since we're teenagers. Back then, we used to hang out like this all the time, just doing goofy stuff. But we now live in separate cities, with wives, kids, jobs, and we never get to do this kind of thing anymore.

17:37Standing around in the middle of the afternoon, laughing in the buff with old friends, feels nice. You're the only one that has a tattoo.

17:48So this is good. We got shirts, and I got a belt. As we exit into the parking lot, our plastic sacks plump with glad rags, something straight-up magical happens. Before getting too excited about what we think we might be seeing, possibly, we await confirmation from the man who can spot a con a mile off. What is a double rainbow? It's legit. A double rainbow. And even Howard's impressed. Wow. Mildly. And so James and I give ourselves over fully. W! Overcome by this fortuitous sign The crew was moved to song Somewhere It was red and purple and crimson and green apple and A rainbow was a good omen Like James' dad Douglas was looking down on us And smiling a big multicolored upside down smile Pink and orange and blue

18:45Sure we were dressed to the 18s but if we each took 45 minutes to sink a ball from two feet away, we might attract suspicion. We needed to train. Hard. I'm talking Rocky, running through waist-high Russian snow hard. A montage of steel drum musicians learning to play chariots of fire set to the tune of Eye of the Tiger hard. I'm talking actually learning how to play golf.

19:18We find a driving range in the fancier part of town and book a golf pro by the name of Stephen. Saturday, 1 p.m. Are you Stephen? Absolutely. Hey, Stephen, I'm Jonathan. Nice to meet you, John. This is Howard. And this is James. This is Stephen. Stephen. A smile with more dimples than the golf balls he lovingly cradles. A tall drink of sports aqua velva eau de toilette, if ever there was. Stephen's been golfing professionally for over 20 years and couldn't be nicer or better smelling and considering the frantic barrage of imbecilic questions we ask he also couldn't be more patient Stephen, can I see the bottom?

19:59Are those official golf shoes? Yeah Well, I have one quick question, Stephen Well, what do golfers think about Happy Gilmore? They find that insulting?

20:09After a brief lecture on the basic how-tos hit ball with stick, hold stick with hands, get ball in hole, we're ready. We insist James go first. After all, this is his mission. What we want to do is we're going to finish it just like this here. While Stephen tenderly positions James' hips and elbows, Howard grabs my microphone and golf commentates. I'd say he looks really, really horrible. Just ridiculous looking. Not encouraging.

20:42Somehow, James manages to connect on his very first try. Everyone's saying very encouraging things, but it's really horrible, just to say. But he got it, it went in the air and he hit it. That's how you say it to a child. It's like, good, you hit it. Stephen looks over at Howard, who now squats in the grass, untying and retying his two left-footed, goodwill-issued golf shoes. And then he looks over at me. A grown man in a too-large Tilly hat, strings cinched tight enough beneath the chin to ensure the clench-jawed vocal affect of a young Catherine Hepburn, he waves us to come hither, offering up something in the way of inspiration.

21:21I'm going to try to make it go from right to left. It must feel really good when you get it up in the air like that. Well, it's great because that's the goal, right, is to get it up. The golf ball flies straight up into the air, and then, as though eerily achieving human consciousness in mid-flight, suddenly takes a sharp left. Wow, so cool! Howard, baptized in the backsplash of Stephen's pheromones, is born again. He's seen the pinnacle of male perfection, and James, it is not. See, James, that's what it looks like. That's when a man hits a golf ball. A male of the species hits a golf ball. Next up is Howard.

22:02He steps to the tee, grips the club in just the way Stephen instructed, does this adorable waddle back and forth to get his footing just so. And then... Did you hear that? Let me play it again. Thrice. A swing and a miss, a swing and a miss, a swing and a miss. That's too much. A little bit. If you're losing your balance, you're swinging. Too fast. The first 25 years are tough.

22:32Oh, Stephen. All this and funny, too. My attempts were just as fruitless. As it turns out, golf is hard. We wonder if Douglas knew just how difficult a mission he'd sent us on. How would we do without a golf pro standing there helping us? You know the difference between golf clubs? There's wet. No, I don't. Not really. I mean, I know. Reg, driver, putter, one iron, two iron, three iron, putter, driver, putter.

23:081.39 a.m. It's the night before the job, and the reality of our situation begins to set in. How can any sting be stung when the would-be stingers absolutely stink at golf? Clearly, this plan wasn't going to work. And so, at a quarter to two in the morning, panic set in. It's impossible. It's impossible for us to play golf. We would suck so hard. We would never make it off the first fucking hole, and if we knocked the balls anywhere... I'm with you. It's like learning how to fucking juggle. It's like it's an incredibly impossible thing to do. It's going to be so obvious that there's something's up because we've never fucking golfed.