By Robert Scucci
| Published 1 hour ago

I’ve never been to a high school reunion. The biggest reason is that I don’t live in the same state, and if I’m going to use my time off, I’m going to do something cool with my family or friends. More importantly, and I think we’re all on the same page here, I know what everybody’s been up to over the last 20 years thanks to social media. Class reunions are pointless in this day and age because I can get anybody’s life story, or at least the parts they share publicly, with a few keystrokes. It’s no longer hot goss if it’s not privileged information, so why bother?

Jack Black’s 2015 effort, The D Train, on the other hand, treats the 20-year high school reunion with the same amount of reverence as Romy and Michele did in the 90s. That movie made sense because the internet wasn’t in every household, and you could totally show up, lie about who you are and what you’ve accomplished, have everybody think you invented Post-Its until you get outed, and then the real humiliation ritual begins. I’d totally show up to that. 

The D Train tries to capture that same energy, but then it veers into increasingly dark territory as Jack Black’s Daniel Gregory spirals into the worst kind of midlife crisis. It’s a funny movie. Everybody does what they’re supposed to do. It’s just that everything would have landed a lot harder if this movie came out in 2005, because that’s where all the humor lives.

It’s Not 2015 Funny, But It Is 2005 Funny

In The D Train, Daniel Gregory is the unofficial chairman of his Pittsburgh high school’s alumni committee. He fancies himself a powerful man in this position, but everybody beneath him knows he’s a joke. He writes long newsletters, often signing off with nicknames he gives himself, like “The D Man,” “D Money,” and, as the title suggests, “The D Train.” Desperate to prove his worth, Daniel is hellbent on making sure his 20-year reunion has the best turnout possible.

While channel surfing one night, he spots former classmate Oliver Lawless (James Marsden) in a Banana Boat commercial, and in his infinite wisdom decides that having a commercial celebrity show up will draw a crowd. Daniel flies out to Los Angeles using company resources after lying to his boss, Bill Shurmur (Jeffrey Tambor), about closing a deal with Oliver. Bill is the kind of boomer boss who “doesn’t do emails,” so he’s incredibly gullible and puts all his trust in Daniel. Certainly this won’t blow back later. Also, it’s 2015, and this whole setup belongs in 2005. It gives off the same vibe as 2013’s The Internship. It’s kind of funny, but it would have been really funny about 10 years earlier.

During his trip to LA, Daniel has a sexual encounter with Oliver, who hooks up with anybody. It’s not that Oliver is actually gay. He’s just promiscuous and takes what he can get, which just so happens to be Daniel, who just so happens to catch feelings.

Oliver comes back to Pittsburgh with Daniel, and their bromance blossoms as they prepare for the reunion. Oliver doesn’t understand Daniel’s infatuation with him. Oliver is the kind of guy who peaked in high school, and I don’t mean that as a jab. Oliver knows he peaked in high school. He lives in a crappy apartment, occasionally lands commercial work, but mostly scrapes by while putting on a brave face.

Daniel is the kind of guy who didn’t peak in high school. In fact, he hasn’t peaked yet. This isn’t a jab either. Daniel has a well-paying job, a nice house, a wife (Kathryn Hahn) who loves him, and he does his best with his teenage son Zach (Russell Posner). He just can’t appreciate any of it because he never left his hometown, which to him feels like something he should be ashamed of. That makes Oliver the coolest guy in his eyes, because he got out and tried to do things his own way. Whether Oliver is successful or not is irrelevant. Daniel feels trapped, and now he’s romantically mixed up with the cool kid from school because he thinks it will give his life meaning.

Jack Black Is Reliably Jack Black In The D Train

The D Train is an effective comedy, but it feels like a “too little, too late” kind of movie. Jack Black is clearly having fun riffing on the material, but the material itself, even in 2015, feels like it’s from a different era. The out-of-touch boss stuff would work better in small doses, but the many misdirects about how CCing on emails works, and how the internet works in general are so heavy-handed that it doesn’t seem real. No guy running a successful company with dozens of employees under him is that clueless, even if he is technologically inept.

The whole high school reunion angle doesn’t work for me either. Grosse Pointe Blank and Romy and Michelle’s High School Reunion made sense because people actually fell out of touch back then. The D Train feels like it’s trying to tap into that same idea without realizing it missed the bus.

What’s really unfortunate about The D Train is that Jack Black is hilarious. He’s reliably Jack Black, and that’s all he needs to be. He’s also more complex than his usual screwball roles because Daniel is working through some seriously heavy emotions. He feels trapped in his life, unfulfilled in his marriage, experiences a confusing sexual awakening in middle age, and just wants to be somebody people talk about. It’s a sad story that’s made funny through over-the-top, and often clueless, characterization.

What’s even sadder is that these very funny people are trying to do very funny things in a world that no longer exists. It didn’t exist when this movie came out, and anybody under 30 watching it today probably won’t understand why a high school reunion matters this much to some people.

The D Train is streaming on Netflix.

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