Tyler’s death at the age of 59 after a three-year battle with cancer was announced on Sunday, sparking many to look back over his career.

While the actor did perform minor roles in other TV shows, from Sabrina, the Teenage Witch to Just Shoot Me, his Friends character is iconic and, other than the main six stars, he was the longest-serving member of the show.

Newsweek looks back at his best moments as Gunther, from his desperate attempts to woo Rachel to his strange exchanges with Joey.

Gunther’s Debut

When tracing Gunther’s debut, it can be difficult as, for many scenes, he was merely in the background, not speaking.

The first word he says is a simple “yes” in the 33rd episode, but it comes in a hilarious moment where his confusion at Ross and Rachel’s relationship is made clear.

In the scene in the second season, Ross buys Rachel a slinky to apologize for his list of pros and cons about dating her, which he compiled while trying to choose between her and Julie.

She is not impressed at this gift, and so, frustrated, Ross gives the slinky to Gunther, after determining the coffee barista has stairs he can use it on.

Gunther Was a Soap Star

Like Joey, Gunther was also a soap star, but died unceremoniously in an unfortunate accident.

In season 2, Joey speaks to Gunther about the death of his character Dr. Drake Ramoray on Days of Our Lives, saying he fell down an elevator shaft.

Gunther surprises Joey by replying: “That sucks. I was buried in an avalanche… I used to be Bryce on All My Children.”

Gunther Keeps the Mouse in the House

During the third season, Phoebe brings her boyfriend to meet the group who, unfortunately, seems unaware that his clothes are revealing more than he bargained for.

While the other friends are aware but scared to mention it (including Phoebe), it falls to Gunther to keep order in Central Perk.

He turns to the new beau and says: “Hey buddy, this is a family place. Put the mouse back in the house.”

Gunther Doesn’t Know the Friends Except Rachel

Despite the friends spending so much of their time in Central Perk, only Rachel managed to make an impression on the coffee shop worker.

In season 4, Joey turns up at the coffee shop and inquires about Chandler’s whereabouts.

Bemused, hilariously Gunther replies: “I thought you were Chandler? Well, one of you is sitting over there.”

Gunther and Mrs. Whiskerson

In season 5, Gunther kindly agrees to take Rachel’s evil cat from her, as a further signal of his love.

Mrs. Whiskerson had scratched her and made her miserable, and Gunther barely even knew what the animal was.

He turns to Ross and asked: “So, what is this? Some kind of snake or something?”

Gunther Insults Ross in Dutch

In season 8, Ross starts learning Dutch, only to be verbally abused by Gunther, who speaks the language fluently.

The barista calls Ross an “ezel,” meaning donkey, causing a furious Ross to return the insult.

But Gunther lands the killer blow with “jij hebt seks met ezels,” meaning “you have sex with donkeys.”

Gunther Finally Expresses His Love for Rachel

In the penultimate episode, Ross spends most of the time planning to tell Rachel he loves her, and doesn’t want her to move to Paris.

But Gunther gets in first, asking whether his love for her might “change her plans.”

Needless to say, Rachel doesn’t give him the answer he wants, but kisses him on the cheek and thanks him for his love, saying she loves him too, but not in the same way.

Of course, Gunther’s best-loved moments tend not to have words at all. Whether it’s gazing lovingly at Rachel or smiling maniacally at Ross’ failings to woo her, the barista was a hugely important part of the Friends fabric.