Jessica Simpson
The most awkward interview on Ellen’s talk show has got to be the one with Jessica Simpson back in 2007. Who can forget how she rambled on and on about off-topic stories like her marriage, her daughter’s birthday party, and even her own uterus?

Clearly, she was not in the right state of mind and even Ellen didn’t know what to do other than give her a strong side-eye. Jessica now admits that she was not sober during the interview and can’t even bear the thought of watching that episode. She has also apologized for her behavior in the book but DeGeneres is yet to respond.