Answer #1
According to the NASCAR.COM website, as of 4-18-2009, Jeff Gordon has the most pole positions for the "modern era."
1 Jeff Gordon - 67
2 Darrell Waltrip - 59
3 David Pearson - 55
4 Bill Elliott - 54
5 Cale Yarborough - 51
6 Mark Martin - 44
7 Ryan Newman - 43
8 Geoffrey Bodine - 37
9 Rusty Wallace - 36
10 Bobby Allison - 36
Answer #2
Richard Petty has 126 Pole wins, for a complete list including active drivers:
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Yes, it has been done nine times.
Here is the list of drivers who won the Daytona 500 from the pole:
Yes, seven drivers won the Daytona 500 from the pole position.
* Not an official pole: In 2004, Greg Biffle was the pole sitter and had to change engines. This gave the number one starting spot to Dale Earnhardt Jr., who went on to win the Daytona 500.
In 2011, Trevor Bayne won the Daytona 500 on his first attempt.
Lee Petty also won on his first attempt; of course his first attempt was the first 500.