Admittedly, the Dead Pool wasn't Eastwood's finest hour, but for the time, it worked. Eastwood has always been a supporter of young actors he feels are up-and-coming/rising stars and tries giving them a leg up.

Liam Neeson, for example, had been acting for less than 10 years, though he'd starred in several films, but before The Dead Pool, the only great film he did was Excalibur in 1981, his 3rd film. Next was 1988 with The Dead Pool, and being recruited by Eastwood for the film booked Neeson's career. Many of his films are low rated, but he's had some stellar ones and amazing opportunities on the back of Eastwood's support.

Similarly, he saw the talent in Jim Carrey and cast him in the film. Interestingly, Carrey has been acting almost as long as Neeson, but hadn't been in any blockbusters until The Dead Pool. Eastwood brought him back in a cameo appearance in Pink Cadillac where he played a lounge performer. Then his career rocketed with Ace Ventura, The Mask, Dumb and Dumber, etc.

Back to The Dead Pool, I personally believe better actors could have been chosen for the roles Neeson and Carrey had. Not sure who, but I didn't think they worked in this context. I love the plotline though...the dead pool game. That will be one of those plotlines other writers won't be able to use except in remakes, which Eastwood is generally strongly against.