Richard Webber is one of Grey's Anatomy's longest-running characters and has been involved in a wealth of memorable storylines. Not only is he the hospital's Chief Medical Officer, but he's also a very skilled surgeon, making him a superior asset to Grey Sloan. Long-time fans of the show will recognize him for his strict demeanor and traditional way of doing things.
Yet, it would be wrong to ignore Webber's infectious sense of humor. Whether he's making a social faux pas or throwing shade at one of his coworkers, this senior surgeon certainly knows how to lighten the mood. As such, fans tend to enjoy his rich blend of funny moments and dramatic tension.
Webber Tries to Show What Tickles His Fancy
Season 6, Episode 18, "Suicide Is Painless”
There's no denying that Grey Sloan is packed full of young professionals, all of whom are eager to enjoy their fair share of dalliances and relations. But Richard Webber doesn't frown upon them for having their fair share of fun. In fact, he tries to fit in with his younger counterparts.
In "Suicide Is Painless", a nurse catches Webber and Karev's eye and the former is keen to express his appreciation for her figure. But, despite his incredible levels of intellect, the Chief stumbles across his phrasing and accidentally comes across as a lot more violent than he anticipated. Fortunately, Karev is there to remind him that the real phrase is "hit that."
The Chief Is Not Exactly Social Media Savvy
Season 7, Episode 13, “Don’t Deceive Me (Please Don’t Go)"
Richard Webber has an abundance of experience in the medical field and is responsible for handling a wealth of superior equipment and tools. But, the esteemed professional has yet to master the art of social media. During "Don't Deceive Me (Please Don't Go)," Webber is keen to keep an eye on Dr. Bailey's social media presence as she tends to post information about her surgeries online.
Dr. Owen Hunt offers his services, but once again, Webber's phrasing makes his intentions seem much more perverse. A lot of fans see this as a great moment between two senior surgeons as it allows Dr. Hunt to sit in the driving seat for a change. Again, this is a prime use of irony, as it seems that Richard Webber can complete a ton of complex surgeries but can't work a simple desktop computer.
His Teammates Are Stunned by His New Look
Season 3, Episode 17, “Some Kind of Miracle”
Though Richard Webber has starred in Grey's Anatomy since 2005, he has always donned his signature gray hair. Yet, in "Some Kind of Miracle," he arrives at work with a new patch of black hair, taking years off of him. Though it may not seem like a big deal to anyone else, his team is very curious as to why he decided to alter his silver fox persona.
While in a crowded elevator, Webber admits that he dyed his hair to make himself more noticeable to the ladies. Admittedly, this is quite a bittersweet moment as fans quickly realize that he's keen to get back on the dating scene after his separation from Adele. In turn, this scene acts as a gentle reminder for the audience as it conveys the idea that Webber still has a personal life and feelings outside his stressful job.
Webber Shows Where His Loyalties Lie
Season 2, Episode 18, “Yesterday”
There's no denying that Derek Shepard and Mark Sloan have their issues, especially since Sloan had an affair with Shepard's ex-wife, Addison. These feuds are nothing new when it comes to Grey's Anatomy, but Richard Webber works to give this awkward conflict a touch of comic relief. In this episode, he doesn't hesitate to show his distaste towards Sloan and even admits to Derek that he didn't want to hire him.
This scene is a great example of how the Chief often lets his professional status slide. It also highlights that he tends to play favorites, something fans may not expect from such a dignified surgeon. Overall, this scene works to show a unique side to Webber, one that doesn't always know when to hold his tongue.
The Chief Knows When to Be Stern
Season 2, Episode 18, “Yesterday”
When it comes to crisis situations, Webber is exceptional at keeping level-headed. But, in "Yesterday," the smallest mishap seems to send him in a spiral. After Derek punches Mark in the face, the first thing Webber is concerned about is whether Shepard's very expensive and skilled hands are damaged.
Even as a surgeon himself, Webber is well aware of just how important hands are for this line of work and isn't willing to lose one of his best surgeons because he doesn't want to put ice on his hand. Plus, it's also quite funny to see this mild-mannered man use expletives like "Damn" so openly. Overall, this scene works to foreshadow Sloan and Shepard's long-running conflict but still manages to sprinkle in some jokes along the way.
Webber Gives Bailey a Back-Handed Compliment
Season 3, Episode 13, “Great Expectations”
A lot of fans enjoy Webber and Bailey's tender relationship, mostly because they've been on the show together since the very beginning. Yet, Richard has a bad habit of putting his foot in his mouth, even when he's trying to be nice to her. In "Great Expectations," Webber tries to explain that he sees her as Chief in the future and respects her intelligence and work ethic.
However, what comes out is a low blow about her height. There's no ignoring Bailey's height, as she famously has to stand on a stool in order to complete her surgeries. As a result, fans can't help but burst out laughing when they notice Richard trying to walk back his comments about Dr. Bailey's lack of height. In turn, this heart-to-heart gone wrong easily establishes itself at the halfway point on this list.
The Chief Doesn’t Hesitate to Fight Back
Season 6, Episode 17, “Push”
As one of the best surgeons in Seattle, it's evident that Webber knows when to pull his foot off the accelerator and takes some time to think. Yet, his squabble with Owen in "Push" suggests that he has a tendency to fly off the handle. Owen makes an innocent remark about Webber's old-school technique, and he immediately receives it as an ageist attack. Though Hunt tries to resolve the issue, Webber quickly swoops in and picks up on his hair color.
These childish remarks work to completely disorientate this professional meeting and present Webber as a juvenile bully. Not to mention, Owen Hunt isn't even really ginger and is probably closer to blonde. So, not only is Webber's comment completely immature, but it's actually quite inaccurate, which is a surprise coming from one of the best surgeons in the world.
Richard Shows His Excitement With an Unusual Phrase
Season 10, Episode 16, “We Gotta Get Out of This Place”
"We Gotta Get Out of This Place" takes place on the Chief's 70th birthday, something he feels pretty insecure about. As a treat, Miranda and Meredith show him a scan of a fetus that suggests that a man has absorbed his own twin. Though he initially tries to hide his excitement, he eventually ends up exclaiming a pretty unique phrase.
Ironically, this line shows Webber's age and makes him stick out like a sore thumb compared to his much younger colleagues. Again, this scene proves that the Chief is still young at heart and still finds joy in new discoveries. Thus, this simple phrase makes Webber seem more like an energetic cartoon character rather than an aging professional in a sea of youngsters.
The Chief Needs a Break Too Sometimes
Season 10, Episode 11, “Man on the Moon”
After being electrocuted at the end of Season 9, Richard spent the majority of Season 10 working to get back on his feet. By the middle of the season, the Chief was finally well enough to go home, but many of his colleagues were convinced that he was going to throw in the towel and put an end to his long-running career. Instead, he reminded his co-workers that he needed a break from them, not from his work.
This line sits at the penultimate spot, but it firmly establishes Richard as a patriarchal figure within the walls of Grey Sloan. In this scene, Webber isn't afraid to put his colleagues back in their place, much like how a father disciplines his children. So, after worrying about him for multiple episodes, fans can find comfort in the fact that he'll never really change his ways.
Webber Showcases His Obscure Teaching Tactics
Season 2, Episode 18, "Yesterday"
There have been a few lines from "Yesterday" throughout this list, and another example sits at the top. After uncovering why Derek punched Mark, Richard Webber is keen to know that the former did the job correctly. It's important for fans to recognize that Richard Webber taught these workers everything they know, so he expects people like Derek to follow in his footsteps and complete work to the highest standard.
So, by asking Derek whether he punched Mark with all his might, he suggests that he's proud of Derek, even if his actions are completely inappropriate. This is quite surprising for some fans, as Webber usually plays by the book and isn't willing to rock the boat in any way. Thus, his pride in Derek highlights how he sees his surgeons as his children and is willing to teach them the difference between right and wrong, no matter what.