The funnyman flirted his way through the interview as he sweet-talked guest presenter Meghan McCain, 24, and show regulars Joy Behar, Whoopi Goldberg and Barbara Walters.
After touching on the topic of Brand's sex addiction and recently being named a U.K. tabloid's Shagger of the Year, the comic told McCain, "You'll have me stripped of my title and I'll have you stripped of your tights!"
But Brand saved his most tongue-in-cheek comments for single Shepherd, telling her: "You look nice. I like these gladiator style shoes and I like these legs. Now, I understand you've been celibate for a while, when are you gonna give that up?"
Shepherd played into Brand's womanising ways, warning him, "Don't start something you can't finish Russell", to which he replied, "I assure you, this is an area where I am confident. I am not bluffing. I will take care of you, I'll make you see multi-colours, I'll make you forget your own name!"