Top 7: Biggest Losers in (Very Recent) Television History

by Kolby Solinsky
Editor, White Cover Magazine


The best characters in any and all television shows are not the main characters. They’re not even the quirky supporting actors or actresses who end up winning the series’ only Emmys. Think Ari Gold, Barney Stinson, or even Karen from Will & Grace.

No, the real winners are the pathetic ones. The ones you take pity on and feel so much shame for. The losers of every television show are the ones you love to see fail. They make you feel great about your own life because — no matter what you’re doing — you are always going to be greater than them. They’re always destined to fail, because they’re just losers.

Here are the Top 7, in no particular order.


Duck Phillips – Mad Men

Nobody captured the desperate, 1960’s fake cool thing better than the uber-pathetic Duck Phillips. His speech. His flirty messages with the only younger woman who would sleep with him (Peggy). His haircut and his suit that all looked like something that would belong to a poor man’s Don Draper. In the end, he’s rubbed out by everyone around him (and rubbed off by no one), and it was all his own doing. His temper and his half-baked notion of what made a real man were intended to embarrass Don, but it only caused Duck’s colleagues and the British firm buying him out to cast him aside (*watch below).

Every time the dude spoke, you could hear the cogs in his head turning and his mind asking itself, “Is this what everyone else wants to hear? Have I played it boring enough so far? Why does everyone keep comparing me to some guy named Romney?”

Duck’s storyline in Season 3 was even more depressing than the Zapruder film of JFK’s assassination.  Oh yeah, Duck also played a pivotal part in that episode, too. He wasn’t on the Grassy Knoll, but he caused just about as much damage to America.

Paul Kinsey – Mad Men

Sorry to tap into two guys from the same show so quickly, but Paul Kinsey was just insanely slapstick and so lethally impotent. He hits on Peggy long after she was trendy (like, Episode 2). He grows out a beard because he wants to seem Bohemian, and then dates a black woman in 1961 because he wants people to notice him and his strained, forced Laissez Faire attitude. He’s not intelligent. He’s not handsome. He’s just a fat guy who can’t hold a job or think of an idea.

Finally, we saw him again in Season 5. He had shaved almost all of his head and was in some kind of yoga cult. Even then, he desperately begged for his real job back.

Poor Paul. Poor us for having to watch him.

Andrew Klein – Entourage

Ari’s business partner Barbara Miller summed it up so well:

“Isn’t that Andrew Klein?”


“No go. The guy’s a loser.”

Everything about him stunk of Valley Girl and short-term marital affairs. Well, he had a big affair, so that’s why. Klein destroyed his marriage by falling in love with a co-worker far younger than him. He then crashed into a plunging rocket of depression and into his own house via his car. He almost blew a signing with Aaron Sorkin, and we all felt better when he finally recovered while sleeping at his office. Of course, next season we learned than he was in rehab for a drug problem.

So, yeah. Klein was actually less fulfilling than the final six seasons of Entourage altogether.

Jimmy Darmody – Boardwalk Empire

This sounds a little odd, yes. After all, Jimmy was pretty awesome. He had balls. He wasn’t afraid of much, and he delivered himself to his own death. He oozed coolness.

Unfortunately, Jimmy was doomed to fail. Actually, everyone on Boardwalk Empire who isn’t based on a historical character is doomed to fail. Doomed to die. They have to die, because Nucky, Rothstein, Meyer Lansky, Luciano, and Al Capone can’t die. Not yet, at least.

For all Jimmy’s awesomeness, he also ditched his career for World War I, became a murdered who never answered for many of his crimes or thefts, married a lesbian artist who he wasn’t in love with, didn’t care for his own son, and ran Atlantic City for a total of 88 minutes before getting his head blown off by his one-time mentor.

Oh, and he boffed his mom. Seriously.

At the end, Jimmy Darmody was a loser. That was the most shocking twist of Season 2, not the bullet through the brain.

Senor/Ben Chang – Community

This one is tough, because Ken Jeong is just too hilarious for anyone to resent him. He dresses like a Cuban cab driver, he faked his way into a job as a Spanish teacher at a community college and was then caught, he lived in the school’s air vents and then in a room behind the cafeteria while working for no pay as Greendale’s security officer, and he had all his clothes stolen from the YMCA while in the shower… twice.

But, really, nobody else on television today epitomizes Loserville like its Mayor, Senor Benjaming Chang.

Smithers – The Simpsons

Does this even require an explanation?

Gabe – The Office

This one seems a little too… small. After all, everyone knows that Steve Carell’s Michael Scott was brutally and hilariously pathetic. But, then again, he got engaged and moved to Colorado to start a new life and everyone cried a little when he took off.

So, in the end, Michael Scott recovered from the Pyramid Scheme scene from Season 2.

Gabe, though, was textbook this list. He hosted a Glee party, he cried repeatedly when Erin dumped him (and then firmly dumped him), and he yelled this at Ed Helms: “Shut up about the Sun!”

He was tall and lanky and resembled a transvestite alien. (Sorry to whoever plays him. I have enough respect for you to not research this on IMDB and re-print it.)