|Other(s)||Henry Best (best friend)|
|First Appearance||Episode One|
|Portrayed By||Robert O'Neill|
|“||I used to have a strict ass, now I've titanium hip.||”|
— Cliff to his friends in Episode One
Cliff Costello is one of the main character of Cucumber.
Cliff's hit middle-age magnificently - drunk, shambolic, chasing after boys half his age, and proud of it. He's both Henry's best friend and his greatest tormentor.
A playboy always looking for new adventures, ready with a joke but also a close friend of Henry who knows inside out. According to Cleo, if you were hiding from someone, ask help from Cliff. He loves spicy stories and dramas, being an avid gossipy.
Cliff is a handsome man with graying hair, a prominent nose, and a nasal voice. Despite being in his forties still, has a well-shaped body.
Because of his alcoholism during his youth, his bones were crushed and he needed to undergo surgery that made him limping, in fact, he needs to walk with crutches.
In Episode One, Cliff is having dinner with Henry, Lance and the rest of their group of friends to whom reveals the outcome of his operation. Alcoholism has crumbled his bones into dust and now is forced to walk with crutches, with his new titanium hip. While outside smoking with Henry, he asks him how is his relationship with Lance since he knows that Henry has a sexual phobia and that very often he may have a very obsessive crush with colleagues at work.
In Episode Two, after receiving a call from Chloe, Cliff does a little research and finds out where Henry has moved and visits him, discovering a party full of hot guys. He then starts flirting with Freddie.
- Cliff is the only Henry's friend who appears in more episodes than the rest of the first episode's gang.