For this reason, we almost overlooked the original rich mom - Lily van der Woodsen. Gasp! One of the most iconic wealthy matriarchs of all time, van der Woodsen (played to perfection by Kelly ...

In a special flashback to the 1980s, before she became a van der Woodsen, Lily Rhodes is kicked out of boarding school and runs away to Los Angeles to reconnect with her parents. Show more In a ...