I have traced the Vandygriff side of the family tree all the way back to The Netherlands, to the van der Grift family. As we travel back in time, the spelling of the surname changes and becomes more Dutch and less Americanized. Below is a simplified version of the tree following the paternal line of Vandygriffs. I've included years and spouses as well.
Brandi Vandygriff (me) 1993 - living : married to Benjamin Pennington 1992 - living
Rufus Irwin Vandygriff 1948 - living : married to Bennie Janel Lokey 1948 - living
Rufus Junior Vandygriff 1923-1965 : married to Betty Louise Mickey 1923-1971
John Elliot Vandygriff 1875-1949 : married to Pernecie Lizetta Rogers 1882-1938
William M. Vandergriff 1856-1908 : married to Elizabeth B. Pennington 1854-1921
James Newton Vandygriff 1809-1870 : married to Rebecca Stanley 1819-1864
Christopher Vandergriff 1781-1869 : married to Mary Uvales 1785 - deceased
Leonard Vandegrift 1754-1821 : married to Martha Pennington 1785-1821
Jacob Vandergrift 1720-1775 : married to Ann Atkinson 1728-1767
Jacob Vandergrift 1678-1754 : married to Sarah Mary Jacobs 1680-1728
Leendert Jacobs Vandergrift 1655-1725 : married to Christina Elsworth 1657-1720
Jacob Leendertszen Vandergrift 1622-1697 : married to Rebecka Fredricks Lubbertsz 1628-1711
Leendert Evertsen Vandergrift 1587-1657 : married to Maritjen Paulwelsdotter 1585-1679
Evert Antonisz van der Grift 1561-1649 : unknown wife/spouse
If you notice, there are three Penningtons mentioned in this short time frame. My husband Ben, my second great grandmother Elizabeth and my 5th great grandmother Martha. However, I have been unable at this time to find more information about Martha and her connection to the Pennington family. Both Ben's Pennington branch and Elizabeth's Pennington branch can be traced back to England, to Gamel de Pennington. The branches do converge at 1595 with William Pennington. Family research is wildly fascinating to say the least.
More weird family things to come in the future. :)