Ranking The Office Bosses By Likability
When the topic of Dunder Mifflin bosses comes up, it usually brings to mind a limited number of individuals. First and foremost, there's Steve Carell as Michael Scott. The long-time regional manager hogged the spotlight for the better part of seven seasons. Yet, the larger-than-life Mr. Scott wasn't the only one to wield power within the four walls of Dunder Mifflin Scranton.
Over the course of nine seasons, 18 different people donned the hat of authority within those sacred, paper-pushing walls — and that doesn't even include the likes of Brian Baumgartner as Kevin Malone, who proudly spun in Andy's chair for a full hour as manager early on in Season 9.
With so many hats thrown in the ring, we've decided to gather up all of the different names and rank them by how likable each character was. Oh, and just to clarify, this will be a general assessment of the character's appeal from the perspective of the audience, not their charisma in the eyes of their subordinates. So, without further ado, here is the official Looper ranking of all of the bosses from The Office, from least to most likable.
Jan Levinson (no Gould)
To kick off the list, we have one of the most detestable characters to ever appear on the show. Melora Hardin's Jan Levinson was in the action from day one, and over the course of time, we got to watch her slowly sink from a high-flying executive to a fired employee with self-destructive tendencies...and then right back to a powerful leader again, this time at the Scranton White Pages.
Throughout her journey in and out of power, Jan exhibited a boatload of terrifying tendencies. She quietly undermined Michael as a coworker and vented her sexual desires on him as a subordinate. Even when she lost her job, she continued to do everything in her power to destroy Michael's life and drive him into bankruptcy. When we finally saw her again, her unspoken deeds with Clark clearly hinted that she still didn't have her darker side under control. At pretty much every turn, Jan made a clear case that she was one of the least likable characters on the show.
Ryan Howard
Ryan Howard was always a very strange member of the Dunder Mifflin aristocracy. Throughout his time as the youngest VP in the company's history, Ryan showed that the power had clearly gone to his head. He developed a severe drug addiction, completely left his "friends" in Scranton in the dust (not to mention his on-and-off girlfriend Kelly) and his misguided website initiative cost the company a fortune, ending up with the man himself getting arrested.
Even when Ryan wasn't a boss, the baby-faced office worker showed a consistent pattern of indifference towards the welfare of those around him. He was judgmental, narcissistic and more than a wee bit smarmy. After a brief foray into the upper echelons of the company that ended in disaster, he showed absolutely no signs of learning from the experience. Instead, he just kept moving along with his self-centered, cutthroat ways. To quote the man himself, "Yeah. Jim is a nice guy. That's why I got the desk."
Charles Miner
Charles Miner (played by Idris Elba) only beats out Ryan because he has a much smaller sample size of "work" to judge him by. When we met the hunky manager in Season 5, Mr. Miner from Saticoy Steel immediately began to cut costs, curb behaviors, and do everything in his power to try to bring the unwieldy Scranton Branch to heel.
As if this heavy-handed management style wasn't already enough to make fans look at him sideways, Charles then proceeded to display a personality that utterly clashed with the "salt of the earth" employees that he was overseeing. The man was cocky, cold-hearted, and particularly antagonistic toward Michael and Jim, which automatically puts him on the wrong side of the ledger for many fans. As his stint on the show played out, Miner slowly came to admit that he didn't know how to inspire the people the was trying to lead. It's a lack of inspiration that is shared by viewers, too.
Alan Brand
The first time we heard about Aland Brand was in the Season 1 episode "Hot Girl," when Jan explained that she and Alan (played by Alan Fudge) came up with an incentive program to help boost sales. On the surface, this seemed like a promising start for the Dunder Mifflin executive. However, in Season 5, we discovered that the man also got paid millions of dollars in stock options for a subpar performance, effectively phoning it in as a top leader in his failing company.
The next time we saw him, Brand was looking rather uncomfortable as he fielded questions from a horde of angry shareholders. Although outwardly keeping his cool, for the most part, he was clearly unsympathetic to the pain and financial damage caused to everyone in the room. The look was definitely not a good one, and when he was cleared out and Sabre moved in, it was hardly a loss that fans got too worked up about.
Robert California
Jim Halpert put it best when he said that Robert California "Creeps me out. But I think he might be a genius."
As portrayed by James Spader, the shifty authority figure first showed up gunning for Michael Scott's original position at the tail end of Season 7. He steamrolled into the picture, captured the title of Regional Manager, and then proceeded to talk Jo Bennett out of her own lofty position in order to make himself the company CEO.
While he only lasted for a little over a season, Mr. California overshadowed the show with his powerful, overtly sexual, and all-around disturbing personality every time he was in a scene. If it weren't for his largely peripheral role, there's little doubt that California would sink much further on this list. However, since we don't see him a whole lot, even in Season 8, he managed to fall on the upper end of the lower half of our rankings.
Ed Truck
Ed Truck (Ken Howard) was Michael's old boss, and we never actually saw the man in action. Still, judging from Scott's extremely biased opinion — which included the words "yuck," "horrible," "he hated fun," and "jerk" — it would appear that Truck was a boss that didn't take any crap from his employees. In fact, many of Michael's managerial decisions stemmed from a direct desire to do the opposite of what Ed Truck would have done — which, to be fair, is just as much a compliment as anything else, just sayin'.
Still, even if he wasn't the worst boss on the planet, the little that we did see of Truck didn't scream charisma. On the contrary, the one time we saw him in the episode "The Carpet" (Season 2, Episode 14) he seemed to be an uptight businessman, with one of his only lines being "You can't expect to be friends with everybody." Add on the fact that he ended up decapitated, and the deck is just too stacked against this guy to get anywhere far on a most likable list.
Deangelo Vickers
At this point on the list, we're starting to get into the realm of bosses that are an interesting mix of likable and detestable. No one sums up that strange dichotomy quite as well as Will Ferrell's Deangelo Vickers. Vickers was the first man to try to step into Michael Scott's shoes as the iconic manager prepared to start his new life in Colorado.
While he was still in training, Vickers seemed like a fairly pleasant guy — even if he did occasionally throw out "dead man walking" jabs when no one was looking. Once Michael was no longer on the premises, though, we started to see a different side of Vicker's strange, bipolar personality emerge. From inner circles to strange sales techniques, sexist overtones, invisible juggling routines and a compulsive need to avoid letting his employees figure him out, it was kind of amazing how quickly Vickers tanked his initial likability under a barrage of strange behavior before abruptly exiting the show.
Gabe Lewis
Picking on Gabe (Zach Lewis) for being unlikable would be like besmirching Toby. It feels too much like kicking a man when he's down. Are there flaws in Gabe's character? Sure. Did he make mistakes? Absolutely. Was he as bad as you'd guess based on how others treated him? No, not really.
That said, there's nothing about Gabe Lewis that screamed "we love this guy!" On the contrary, Gabe is about as pathetic a character as you can find this side of the Central Scranton Expressway. He utterly lacked authority, and was a constant butt of jokes. His attempts at leadership were laughable, and his taste for the Cinema of the Unsettling was simply too far for most. While Gabe was hardly the least likable person on the show, his pathetic nature sparked a certain degree of sympathy at times. However, there was very little out there to help him rise above a level of un-compelling mediocrity.
Jolene "Jo" Bennett
Jo Bennett (played by Kathy Bates) was one of the more powerful bosses to ever step foot on the Dunder Mifflin Scranton premises. The character was a self-made businesswoman whose printer empire, Sabre, scooped up the successful branch as the rest of Dunder Mifflin floundered. Years later, Bennett is an interesting person to rank on a list based on likability. Working against her is her cold, calculating business attitude. She wasn't afraid to make tough decisions, like demoting a co-manager, and could lose her temper at times.
Even so, Jo's calculated business moves could also be interpreted as an attractive sign of strong womanhood. From there, her accolades begin to pile up. She's a breast cancer survivor, can fly a plane, and even narrates her own autobiography. Add onto that her sunny southern personality, her penchant to call people by bubbly nicknames, and her use of regionally-out-of-place phrases, and Bennett easily lands firmly in the middle of these rankings.
Robert Dunder
This next one is a treat. That's right, we get to rank one of the founding fathers of Dunder Mifflin, Mr. Robert Dunder himself (as played by John Ingle). The 87-year-old retiree showed up in Season 4 when Michael invited him as a countermeasure to what he perceived as Ryan's threat of ageism. During his visit to the Scranton branch, we found out that the "Old Fart" met his partner Robert Mifflin through a Rotary Club — although in the Season 5 episode "Company Picnic," it's also claimed that they met during a tour of Dartmouth College.
Either way, the aged Mr. Dunder proved to be an amicable chap that was more than willing to share stories about his past. While he was hustled out of the meeting before we got to see more of him, we found out enough about the pleasant fellow to at least rank him in the top half of the most likable bosses.
Karen Filippelli
Karen Filippelli (played by Rashida Jones) was one individual who technically counted as a boss, even though she never got directly put in charge of the folks in Dunder Mifflin Scranton. After a brief period of time spent working as a sales rep in the Scranton branch, Karen started a new, post-Jim phase of her life when she headed up to manage the Utica branch of the company.
The next time we saw Karen, she seemed to be thriving as a manager. She clearly did well, because when Michael visited yet again in Season 5, Karen was still there, and even happily pregnant this time. While Karen and Jim were never a great fit, that didn't change the fact that Filippelli was a hard worker and appeared to be a solid boss. She always handled issues with authority and even patched things up with Pam before all was said and done. While she isn't the most likable, she definitely gets a solid grade.
Andy Bernard
Ed Helms' Andy is another tough character to rank by likability — particularly as a boss. If you were to rate the man purely based on his leadership qualities, he would be a bit lower. After all, his entire time as Regional Manager of the Scranton Branch was spent scrambling, and it ended with his quitting to pursue an ultimately failed career in acting.
That said, when you back out and consider Andy's entire Office tenure, he does manage to inch a bit higher up on the list. Sure, he started out as a total jerk in the Stamford branch, but following anger management, the man became something akin to a model citizen. The hot and cold aspects of Andy's likability naturally make it hard for him to fall too much in the rankings. But the character still did manage to endear himself to millions of fans, both in real life and, as we saw in the finale, even in the show itself.
Nellie Bertram
Nellie Bertram (Catherine Tate) was an interesting anomaly, even in an office filled with strange and exotic forms of leadership. The businesswoman was a friend of Jo Bennett, and initially took a shot at the manager position when she was seen interviewing for Michael's position — promising more cubicles, less cubicles, and massages to boot.
Bertram popped back up in Florida, where she led the failed Sabre store project before finally weaseling her way into the manager's chair by, well, sitting in it. Bertram's time in power was strange, and it didn't last long. She also caused who knows how much damage by giving everyone unexpected, un-budgeted raises to try to win their loyalty. All the same, Bertram's indefatigable positivity, sunny smile, English accent, and fear of tacos with eyes all add up to make her one of the more enjoyable characters to ever lead the fearless Dunder Mifflinites into the war of work.
Creed Bratton
BOBODDY. Need we say more?
Creed Bratton (as portrayed by Creed Bratton) had an insane rap sheet. The man was a criminal of the highest order. He had no morals, was lazy, and got more than one of his co-workers fired. Yet, we love him. Over the course of the show, the Quabitty Ashwoods rep put on an endlessly entertaining reel of quirky behavior. This only got cranked up to 11 when he was bumped to the position of acting Manager late in Season 7 purely on the grounds of seniority — like, really, there was no other reason.
During his time as leader, Creed showed a humorous string of attempts to rally the office in a time of transition. He brainstormed acronyms and called random team-building meetings without warning. He also attempted to undermine the company and set up his own enterprise as a competitor. All in all, Creed's time as leader was hilarious, ridiculous, and just another part of the Creed Bratton complex that we all know and love so well.
Dwight K. Schrute
Rainn Wilson's Dwight was another hot and cold character when it came to likability. The dude was riddled with upsetting statements, strange behaviors, and all sorts of outlandish character traits that made him anything but appealing.
Nevertheless, over the course of nine seasons, we saw the beet farmer slowly transform into a genuine leader and a loyal friend. When he got his first chance as a boss, he literally went down guns with guns blazing. Nevertheless, Dwight's tenacity (which is another of his endearing character traits) ultimately led him back to the pinnacle of the Dunder Mifflin Scranton power pyramid. When the dust finally settled, it was hard to debate the notion that Dwight managed to flip the likability meter on its head. He had gone from a pent-up, frustrated salesman whose primary goal was to defeat his arch-nemesis desk mate to a well-rounded boss that made tough decisions but also cared for his staff.
Jim Halpert
Is Jim Halpert (as portrayed by John Krasinski in the role that made him a household name) perfect? Certainly not. And yet, who doesn't love the guy? The office wiseguy came to power early in Season 6 as he was elevated into the role of co-manager. From there, he proceeded to take on the day-to-day operations of the branch, doing his level best to curb the eccentric behaviors of his partner in power, Michael Scott.
Now, Jim was never particularly enamoring as a boss. In fact, some of his least likable moments took place when he was operating as a manager. Still, Jim did a decent job helping to guide his coworkers through a very turbulent transition as they became a part of the Sabre Family. Taken as a whole, Halpert's personality was always dependably pleasant, witty, and relatively easygoing. There's a good reason he became one of the most popular characters on the show, and it should come as no surprise that he now manages to land so high on the list.
Michael Gary Scott
There's a solid case to be made for Michael to be at both the top and bottom of this list.
On the one hand, the man was always an absolutely abysmal boss. He refused to make tough decisions, incessantly insulted his employees and behaved with the impulsive reactions of a child.
On the other, we can't help but put him higher on the list, even if we don't think he deserves the top spot. Over the course of the show, Michael's character arc was nothing short of fantastic. From his low beginnings as a jerky, insecure manager, the man slowly evolved into a leader that truly won the hearts of his people, many times in spite of themselves. When you throw in the countless endearing little moments that surrounded his character, it was difficult to disagree with Jim when he pointed out: "What a great boss you turned out to be. Best boss I ever had."
David Wallace
Ladies and gentlemen, we present to you our dark horse candidate for "most likable boss," none other than David Wallace (Andy Buckley) himself.
When you break things down, Wallace was the one character that quietly yet easily took the cake when it came to likable bosses. The CFO sat at the pinnacle of the Dunder Mifflin power pyramid and ended up being the epitome of the old phrase "speak softly and carry a big stick." He repeatedly showed the audience that he was in his position for a reason. He axed branches early in the show, and was seen reprimanding Michael more than once.
That said, he also had the soft-spoken schtick down pat. The overwhelming majority of times that Mr. Wallace entered the building, he was the picture of kindness and respect. He listened to his employees, accepted feedback and suggestions with grace, generally kept his cool even in tough situations, and managed to constantly wear a smile. While it isn't everything, David Wallace's ability to stay calm and collected (well, at least most of the time) goes a long way and lands him the top spot on our list.