Not always. If you were 45 and entered the market in 2008, you'd be in a great shape now, probably better than a 20 year old who entered the market in 1999.
This is only possibly true if the 20 year old made his sole contribution in 1999. The more reasonable case is the 20 year old made his first contribution in 1999, and now has 13 years of contributions plus gains.
It's highly unlikely that 3 years of gains from 2008-present would outstrip 13 years of contributions + gains + reinvested dividends.
It's highly unlikely that 3 years of gains from 2008-present would outstrip 13 years of contributions + gains + reinvested dividends.