According to Tony Soprano, a “happy wanderer” is a guy walking down the street with a clear head who’s “always f*ckin’ whistling.” Which character, or characters, on The Sopranos would fit that profile? There’s no one right answer to this question, but it’s something to consider as we go through the episode. So, with that said, let’s take a look at The Sopranos, season two, episode six, “The Happy Wanderer.”
The Books Are Closed on New Happy Wanderer Membership
First, it doesn’t take long in “The Happy Wanderer” to conclude Tony Soprano doesn’t fall into this category. In fact, when he sees Dr. Melfi, Tony comes right out and tells her that he feels like he’s “a f[]ckin’ loser.” I suppose this should come as no surprise given the Soprano family toxicity that’s surrounded Tony for decades.Â
Even so, what happened to the boss’s “honeymoon period”? (Junior technicality notwithstanding.) Isn’t that the ultimate prize? Now Tony can relax a little and have others deal with the daily agita, right? Not so fast. Aside from being a government target, one can’t just flip a switch after decades and turn off the part of their brain that’s wired to look for threats. And both Richie Aprile and Tony’s sister, Janice, surely add fuel to that fire in Tony’s psyche.Â
"Some People Are So Far Behind in The Race, They Actually Believe They're Leading."
Speaking of family dysfunction, let’s talk about Eckley. “Who the f*ck is Eckley?!” Tony’s uncle, that’s who. While accompanying Junior to the doctor’s office, Junior reveals that he and Johnny Boy had a brother. And not just any brother. A brother with developmental disabilities. There’s surely alot to unpack there. Though we don’t learn more about Eckley, Junior’s disclosure is another illustration for Tony of how much he doesn’t know.
Warning: Keep Away from Executive Game

In fact, just as Junior notes, it takes a certain kind of player to handle the executive game. What happens to those who can’t handle it? Apparently, if you’re a “respected businessman” like Davey Scatino, you can find a way in. Not surprisingly, Davey learns the hard way about the price of admission to the executive game. The total cost in Davey’s case is 45 boxes of ziti and a close encounter with Richie Aprile.
To be clear, Tony undoubtedly takes advantage of a whole lot of people on The Sopranos. With that said, it’s hard for me to fault Tony for getting frustrated with Davey’s behavior here. He throws cold water multiple times on Davey’s request to come to the game in the first place. Nevertheless, these warnings are no match for Davey’s compulsion to gamble.Â
The Executive Game = Pure Sopranos Comfort Food for Me
As a matter of fact, in addition to borrowing 45 boxes of ziti ($45,000) from Tony for the game, Davey already owes Richie Aprile over eight grand from another game. After Davey gives Richie an envelope that’s “2Cs shy,” Richie warns Davey to pay him back in full before going to any more games. So when Richie shows up at the motel and sees Davey playing, we know it’s not going to end well. Fortunately, Tony intervenes, but not before scaring off the “civilian” players.Â

"Everything this family has comes from the work I do!"

Unfortunately, the consequences of Davey’s compulsive gambling spill over to his family when Davey gives his son’s Jeep to Tony as partial debt repayment. What’s worse is that Tony then gives the car to Meadow, who’s very close with Davey’s son, Eric.Â
Of course, it takes about five seconds for Meadow to recognize the car as Eric’s. When Meadow asks Tony if Eric’s dad sold him the car, Tony’s eloquent response is “Yeah…something like that…you know.” Yes, she certainly knows, and that’s the problem. However, as opposed to mealy-mouthing, Tony doubles down and tells Meadow the cold, hard truth, for better or worse.
Meadow's no fan of happy wanderers, either.
In addition to their mutual connection to the Scatinos, Meadow also shares Tony’s contempt for her own “happy wanderers.” Here, I’m referring to Rachel Weiss when Meadow finds out Rachel got accepted to Wesleyan. I don’t know anything else about Rachel Weiss, and she may not be happy at all. What I do know is that Meadow’s frustrated over someone else’s success, just like Tony was at the guy whistling with a clear head. To be frank, we’ve all felt similar pangs of jealousy or envy at one point or another, but I feel it’s still worth pointing out here.

The Absurdity of Life as Illustrated by Uncle Tom's Father
Aside from Davey and the executive game, one core message on The Sopranos is that life is absurd. What makes Uncle Tom’s father’s death such a strong illustration is the irony of how it happened. Apparently, this guy was an honest, hardworking man who did right by his family. Perhaps he was even one of those special happy wanderers. But doing the right thing provides him no protection against falling off the roof to his death one day after his retirement. Talk about being dealt a crappy hand, huh? (This makes me think of Carmela’s father, Hugh, who survives a fall off a roof in season five).
Consequently, I can’t help but feel cynical when thinking of the millions of good people who face similar tragedy. I think humanity needs to negotiate with the universe for some sort of karmic pension, don’t you think? Otherwise, can you really even be a “happy wanderer” without, as A.J. describes in season six, having “your head wedged so far up your ass that all you could see is your own stupid face”? Still, maybe it’s better than the alternative of existential dread. I’m still trying to figure that one out myself. We can table that for now.
Sopranos Specialty #2: Dualities of Good/Evil and Light/Darkness

Another core Sopranos theme is the duality of good and evil, which is often illustrated through light and darkness. “The Happy Wanderer” presents it in multiple places, but my favorite instance is here with the sky. As we transition from darkness to dawn, we also transition from the executive game to Meadow leaving for school. Not to mention that the song Meadow and Eric are practicing is called “Sun and Moon.”
To conclude, The Sopranos “The Happy Wanderer” (S2, E6) features that special Sopranos combination of laughter, agita, and dread. And what about the happy wanderers? Maybe Uncle Tom’s dad, at least until his untimely death, but who else? It’s tough to make that call, but if I had to, I’d go with Sunshine and Sinatra. What about you? Let’s connect. I’d love to hear your thoughts!
Miscellaneous Laughs and Observations

–Silvio’s outburst upon seeing Matt Bevilaqua sweep away cheese crumbs by his feet.
-Meadow actually “lucks out” when Eric has a meltdown and leaves the concert (this reminds me of Tony’s good luck after killing Christopher).
-Furio’s request for “a lot of clean towels” at the motel reminds me of Livia telling Janice she’s happy to go back to Green Grove because they give her fresh towels every day.
-Oh yeah, Livia’s a bit of a wanderer herself.
-When Richie tells Tony he’s not supposed to smoke inside the funeral home, Tony turns and looks at Uncle Tom’s dead father in the casket and said “Do you mind? I don’t think he minds.”
-When Richie says “Hooo, Johnny Sack! Must’ve had free tokens at the tunnel!”
-Paulie Walnuts telling the cop to stop talking about his family because he’s got his “own f*ckin problems.”Â
-Matthew Bevilaqua is such a fool. He calls Tony “T” at the executive game when he barely knows Tony. (He does that again right before Tony and Puss kill him, too.)
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