Final answer:
The correct answer is 'd. Winning' as it references Charlie Sheen's famous catchphrase and relates to his public persona.
Step-by-step explanation:
The question 'Most likely to try _________ with Charlie Sheen?' is an entertainment or pop culture related query rather than an educational one. Since it involves the actor Charlie Sheen known for his colorful personality and quotes, the phrase 'winning' is often associated with him due to his famous use of the term during interviews.
Therefore the correct answer to fill in the blank would be 'd. Winning' as it's a nod towards Sheen's catchphrase and not necessarily meant to be taken literally in the context of an activity.