Bob Odenkirk Appearances on ‘How I Met Your Mother,’ Ranked

HIMYM needs a comedy boost? Better call Odenkirk
Bob Odenkirk Appearances on ‘How I Met Your Mother,’ Ranked

How I Met Your Mother was one of the last of its breed — the crazy-successful,  laugh-track-fueled network sitcom. But forget the show’s titular secret. What we really want to know is How They Convinced Bob Odenkirk to Do HIMYM. Don’t take that the wrong way — there’s nothing shameful about doing multiple cameos on one of television’s most popular comedies. But in that 2008-2012 era when he occasionally showed up as Marshall’s a-hole boss Arthur Hobbs, remember the other roles Odenkirk was taking on. When he wasn’t mocking shows like HIMYM in bizarro comedies like Tim and Eric’s Billion Dollar Movie and similar Adult Swim madness, he was laying the bricks for Better Call Saul over on Breaking Bad

In comparison, Arthur Hobbs is pretty traditional stuff. In the hands of a lesser actor, we wouldn’t be having this conversation, and not just because Odenkirk is famous. Hobbs as originally conceived was a pretty one-note dude — a bellicose boss who followed Marshall from a law firm to a bank with a tyrannical management style that could best be summed up as “screaming and firing.” But over the course of sporadic appearances over six seasons, Hobbs showed so many more comic dimensions that we find ourselves wondering why HIMYM didn’t use him more often. 

Here are all eight of Odenkirk’s How I Met Your Mother appearances, ranked… 

‘Garbage Island’ (Season 6)


Marshall decides to withhold sex from Lily until he can do something about this damn environment! Sure, shutting out one’s spouse in the bedroom usually fixes global eco-catastrophes. Marshall makes a big presentation to the management team at Goliath National Bank to propose a green initiative. Bossman Hobbs nixes the $12 million program, citing the company’s previous efforts. Although the last time they tried something like this, Hobbs did get to meet Sting. 

Bays & Thomas Productions

No need to spend $12 million when you've already met Sting.

Not much to see here. Now that Hobbs has been established in earlier episodes, there’s little for him to do except ax an executive who agrees with Marshall. A blip of a cameo, this one just doesn’t deliver on the Odenkirk front. 

‘Last Cigarette Ever’ (Season 5)


Marshall and Hobbs meet again. After their relationship ends on a sour note at a law firm in Season Three (see “Chain of Screaming,” below), Hobbs returns as Marshall’s new boss at Goliath National Bank. If Marshall is nervous, he shouldn’t be — Hobbs doesn’t remember his name. Hoping to get off on a better foot this time, Marshall joins Hobbs on the bank’s rooftop to grab a couple of smokes. Good idea, until the cigarettes give Arthur a heart attack. Another brief appearance for Odenkirk, but the guy does a convincing grabber.

Bays & Thomas Productions

You're a fool if you think smoking is cool. A message from the American Cancer Society.

‘Natural History’ (Season 6)

A brief appearance at a swanky bank party gives Hobbs the chance to introduce Marshall and Barney (and us) to the Captain. Fun fact: Hobbs and the Captain were in a college production of Guys and Dolls, with the Captain as Nathan Detroit and Hobbs as assistant stage manager. Hobbs is weirdly out-of-character here as he proudly presents Marshall and Barney as “the future of this company.” He’s not normally this nice. Hobbs sort of makes up for it in the final scene when he catches Marshall working at his desk at 3 a.m. Since it’s so late, Hobbs tells him, “You might as well not even go home.”

‘The Chain of Screaming’ (Season 3)

Here’s the episode where we meet Odenkirk’s “Artillery Arthur” Hobbs, the boss who storms into underling offices with both guns a-blazing. Marshall’s first encounter with his new boss is pleasant enough, but soon he hears Artillery Arthur tearing coworker Ferguson a new one. It doesn’t take long for Hobbs to come for Marshall, an attack that inspires Marshall to burst into tears. 

All this hostile shouting is new territory for Marshall. Barney advises his friend to scream as well, which doesn’t go so hot. Not only does Marshall lay into Hobbs but he quits his job in the process. Artillery Arthur doesn’t mind the tirade, mainly because Marshall quitting means the law firm won’t owe him severance pay. Odenkirk as Arthur Hobbs is cold-blooded, brother!

‘Canning Randy’ (Season 6)

Finally, we get to know a little more about Hobbs the man. He has a wife, Darlene, and an indeterminate number of unnamed kids. But the real love of his life is his dog, Tugboat. The pooch even makes an appearance in a GNB feel-good promotional video. Despite revealing a bit of his softer side, Hobbs is still an asshat — he fires a dude because they’re wearing similar green neckties. Marshall is getting through to his boss, however. After firing Randy (wannabe-brewmaster Will Forte), Marshall convinces Hobbs to give Randy another chance. People, like dogs, sometimes just need to be fixed. There seems to be a human being inside Hobbs somewhere, even if it can only be accessed via Tugboat. 

Bays & Thomas Productions

A horrible man's best friend

‘The Perfect Cocktail’ (Season 6)

More than any other episode, “The Perfect Cocktail” gives Hobbs a chance to flex his meanie muscles. When Marshall quits Goliath to pursue his dream of becoming an environmental lawyer, Hobbs is uncharacteristically understanding. He even makes Marshall promise to list him as a reference. But the bitter Hobbs only wants the opportunity to lie to Marshall’s prospective employers. 

What’s Hobbs’ idea of a “recommendation”? He tells one firm that Marshall yells “Screw the environment!” around the office, parading around sans pants and sporting a “THUG” tattoo. “We fired him when we caught him clubbing the seal in his office with the even cuter seal,” Hobbs confides to one rival. “The guy’s a maniac. He’s just an awful, flatulent racist.” 

Adding “flatulent” was a nice touch. 

Bays & Thomas Productions

Remembering 2011s short-lived sleeveless sport-coat fad.

‘Landmarks’ (Season 6)

Odenkirk is at his best when portraying Hobbs at rock bottom. He’s now divorced from Darlene, who devastatingly got Tugboat in the settlement. Sure, Hobbs has a new dog, but the replacement canine is a bitter disappointment, nothing more than a cheap facsimile: “You’re not Tugboat. You’ll never be Tugboat!” (The poor stand-in doesn’t even get the dignity of a name.) All of this angst might be partly behind his threat to fire Barney if Ted submarines plans for Goliath National Bank’s new headquarters.  

Bays & Thomas Productions

The dog so disgraceful it doesnt even get a name.

Later, the gang runs into Hobbs attempting to get his new dog to do its business. Marshall gives the distraught Hobbs a hug, which seems to make him feel better. Not like “getting Tugboat back” better, but better. 

‘The Pre-Nup’ (Season 8)

We’re ranking this Hobbs appearance at the top mainly because he’s given so much to do — but we admit that the character is all over the place in this episode. First, he has relationship advice for Barney as he prepares to marry Quinn: “Get a prenup, or I’ll neuter you before she ever has a chance!” You can see Hobbs’ point-of-view here: His divorce went so badly, Darlene got Tugboat and one of Hobbs’ kidneys while he ended up with full custody of the kids. Hobbs helps Barney prep the document himself, a stack of papers at least a foot high. An irate Quinn makes a legal doc of her own. 

Soon, all four of the show’s couples are fighting in a boardroom at Goliath, because, you know, it’s a sitcom. Then Hobbs, the guy who threatened to neuter Barney if he didn’t make a list of demands, decides the fighting has to stop: “Enough, enough! You all have someone who loves you, and you’re screwing it up and over what? Who has the most power? That’s not love. Love is trusting someone enough to tell them what’s really bothering you. So that’s what we’re going to do.” 

Somehow, this completely out-of-character advice solves eight people’s love problems in about 60 seconds of screen time. Because again, you know, it’s a sitcom. Hobbs has now completely transformed through some offscreen character growth that we can’t quite understand. “Honesty and vulnerability. That’s love!” he proclaims. Now that he’s realized that he never said I love you enough, he calls Darlene — and asks her to put Tugboat on the line. 

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