Born 1867/69 - His tombstone says he was born in 1869, but in June 1870 he was listed on the census as 2 years old, which would mean he was born in 1867.
1900 in Howell Co, Mo

Howell County, Mo marriages:
Jolliff, Willis F. & Kimbrough, Sarah A. - 28 Dec 1888
See: http://www.howellcountymo.com/HowellCountyMarriages/HowellCo_Marriage_66_-_89_Groom_J_-_M.htm

1900 Mo census - Howell Co, Benton twp, p. 21
Jolliff, Willis (head) - 31, b Sept 1868 IL, m 11 yrs, par b IL
. . . . . Sarah (wife) - 30, b Sept 1867 MO, m 11 yrs, 4 ch/3 liv, par b IL
. . . . . Daniel B. (son) - 4, b Oct 1895 MO
. . . . . William N. (son) - b Nov 1899 MO

1920 Oregon Co, Mo, Highland twp, p58
Jolliff, Willis F. - 51 IL
. . . . Sarah D. (wife) - 51 IL
. . . . Nora (daug) - 28 Mo
. . . . Noel (son) - 20 Mo
. . . . Leora (daug) - 10 Mo
next door was brother-in-law Duke Hosea Kimbrough

Missouri death certificate:
Willis Francis Jolliff, 71, retired farmer, married
born Sept 26, 1869, Illinois
father: Orasmus Jolliff, b IL
mother: Martha Waymon, b IL
wife: Lorine Jolliff, age 64
died Mar 18, 1941, West Plains, Howell Co, Mo
of hepatic cirrhosis, Dr. Thornburgh, West Plains
buried Mar 19, 1941, Jolliff cemetery
undertaker: Robertsons, West Plains
informant: Mrs. W.F. Jolliff, West Plains

Find A Grave Memorial# 15497863
http://www.findagrave.com/cgi-bin/fg.cgi?page=gr&GRid=15497863

• Married: 28 DEC 1888 in Howell Co, Mo

1. Nora Violet JOLLIFF b: 11 APR 1891 in Missouri
2. Daniel B. JOLLIFF b: 2 OCT 1894 in Moody, Howell Co, Mo
3. William Noel JOLLIFF b: 8 SEP 1899 in Missouri
4. Leora JOLLIFF b: ABT 1910 in Missouri

• Married: 3 DEC 1926 in Howell Co, Mo

• Married: 17 JAN 1928 in Howell Co, Mo

• Married: 3 APR 1929 in Howell Co, Mo