Shawn competed in the most competitive era in bodybuilding. This is how he did in the biggest show.
Shawn Ray
1988 Mr. Olympia – 13th Place
1990 Mr. Olympia – 3rd Place
1991 Mr. Olympia – 5th Place
1992 Mr. Olympia – 4th Place
1993 Mr. Olympia – 3rd Place
1994 Mr. Olympia – 2nd Place
1995 Mr. Olympia – 4th Place
1996 Mr. Olympia – 2nd Place
1997 Mr. Olympia – 3rd Place
1998 Mr. Olympia – 5th Place
1999 Mr. Olympia – 5th Place
2000 Mr. Olympia – 4th Place
2001 Mr. Olympia – 4th Place
This is how Dexter did in a less competitive era in Olympias.
Dexter Jackson
1999 Mr. Olympia, 9th
2000 Mr. Olympia, 9th
2001 Mr. Olympia, 8th
2002 Mr. Olympia, 4th
2003 Mr. Olympia, 3rd
2004 Mr. Olympia, 4th
2006 Mr. Olympia, 4th
2007 Mr. Olympia, 3rd
2008 Mr. Olympia, 1st
2009 Mr. Olympia, 3rd
2010 Mr. Olympia, 4th
2011 Mr. Olympia, 6th
2012 Mr. Olympia, 4th
2013 Mr. Olympia, 5th
2014 Mr. Olympia, 5th
Though Dexter has the Olympia win and an overall better competition record. A valid argument can be made that Shawn was a better bodybuilder. He's more complete than Dexter. If you put them next to each other you begin to see the wholes in Dexter's physique. I'd rather look like Shawn Ray but have Dexter's record.