I don't know if threads like this are allowed, but this was something I have been thinking about for a while.
Here are the ones I can think of for each generation starting with the Silents:
Silent Generation:
Pol Pot (b. 1925)
James Earl Ray (b. 1928)
James "Whitey" Bulger (b. 1929)
Jim Jones (b. 1931)
Louis Farrakhan (b. 1933)
Dianne Feinstein (b. 1933)
William Luther Pierce (b. 1933)
Charles Manson (b. 1934)
Saddam Hussein (b. 1937)
Maxine Waters (b. 1938)
David Lane (b. 1938)
John Wayne Gacy (b. 1942)
Baby Boomer:
Ted Bundy (b. 1946)
Hillary Clinton (b. 1947)
Edmund Kemper (b. 1948)
David Duke (b. 1950)
James Hodgkinson (b. 1950)
Harvey Weinstein (b. 1952)
Stephen Paddock (b. 1953)
Mark David Chapman (b. 1955)
John Bachtell (b. 1956)
Osama Bin Laden (b. 1957)
Jeffrey Dahmer (b. 1960)
Yolanda Saldivar (b. 1960)
Generation X:
Malik Zulu Shabbaz (b. 1966)
Timothy McVeigh (b. 1968)
Mohammed Atta (b. 1968)
Cory Booker (b. 1969)
Paul Nehlen (b. 1969)
Quannel X (b. 1970)
Matthew Hale (b. 1971)
Wade Michael Page (b. 1971)
Kristian "Varg" Vikernes (b. 1973)
Jared Fogle (b. 1977)
Rachel Dolezal (b. 1977)
Richard Spencer (b. 1978)
Linda Sarsour (b. 1980)
Mark Collett (b. 1980)
Millennial:
Eric Harris (b. 1981)
Dylan Klebold (b. 1981)
Anita Sarkeesian (b. 1983)
Jason Kessler (b. 1983)
Seung Hui-Cho (b. 1984)
Nathan Damigo (b. 1986)
Omar Mateen (b. 1986)
Colin Kaepernick (b. 1987)
Jared Lee Loughner (b. 1988)
Travis Reinking (b. 1989)
Christopher Harper Mercer (b. 1989)
Aaron Hernandez (b. 1989)
Inna Shevchenko (b. 1990)
Devin Patrick Kelly (b. 1991)
Matthew Heimbach (b. 1991)
Elliot Rodger (b. 1991)
Adam Lanza (b. 1992)
Dylann Roof (b. 1994)
TJ Lane (b. 1994)
Joshua Ryne Goldberg (b. 1995)
Generation Z:
James Alex Fields (b. 1997)
XXXTentacion (b. 1998)
Nikolas Cruz (b. 1998)
Thomas Rousseau (b. 1998)
Trippie Redd (b. 1999)
Anissa Weier (b. 2001)
Morgan Geyser (b. 2002)
Danielle Bregoli (b. 2003)
Kaia James (b. 2006)
Here are the ones I can think of for each generation starting with the Silents:
Silent Generation:
Pol Pot (b. 1925)
James Earl Ray (b. 1928)
James "Whitey" Bulger (b. 1929)
Jim Jones (b. 1931)
Louis Farrakhan (b. 1933)
Dianne Feinstein (b. 1933)
William Luther Pierce (b. 1933)
Charles Manson (b. 1934)
Saddam Hussein (b. 1937)
Maxine Waters (b. 1938)
David Lane (b. 1938)
John Wayne Gacy (b. 1942)
Baby Boomer:
Ted Bundy (b. 1946)
Hillary Clinton (b. 1947)
Edmund Kemper (b. 1948)
David Duke (b. 1950)
James Hodgkinson (b. 1950)
Harvey Weinstein (b. 1952)
Stephen Paddock (b. 1953)
Mark David Chapman (b. 1955)
John Bachtell (b. 1956)
Osama Bin Laden (b. 1957)
Jeffrey Dahmer (b. 1960)
Yolanda Saldivar (b. 1960)
Generation X:
Malik Zulu Shabbaz (b. 1966)
Timothy McVeigh (b. 1968)
Mohammed Atta (b. 1968)
Cory Booker (b. 1969)
Paul Nehlen (b. 1969)
Quannel X (b. 1970)
Matthew Hale (b. 1971)
Wade Michael Page (b. 1971)
Kristian "Varg" Vikernes (b. 1973)
Jared Fogle (b. 1977)
Rachel Dolezal (b. 1977)
Richard Spencer (b. 1978)
Linda Sarsour (b. 1980)
Mark Collett (b. 1980)
Millennial:
Eric Harris (b. 1981)
Dylan Klebold (b. 1981)
Anita Sarkeesian (b. 1983)
Jason Kessler (b. 1983)
Seung Hui-Cho (b. 1984)
Nathan Damigo (b. 1986)
Omar Mateen (b. 1986)
Colin Kaepernick (b. 1987)
Jared Lee Loughner (b. 1988)
Travis Reinking (b. 1989)
Christopher Harper Mercer (b. 1989)
Aaron Hernandez (b. 1989)
Inna Shevchenko (b. 1990)
Devin Patrick Kelly (b. 1991)
Matthew Heimbach (b. 1991)
Elliot Rodger (b. 1991)
Adam Lanza (b. 1992)
Dylann Roof (b. 1994)
TJ Lane (b. 1994)
Joshua Ryne Goldberg (b. 1995)
Generation Z:
James Alex Fields (b. 1997)
XXXTentacion (b. 1998)
Nikolas Cruz (b. 1998)
Thomas Rousseau (b. 1998)
Trippie Redd (b. 1999)
Anissa Weier (b. 2001)
Morgan Geyser (b. 2002)
Danielle Bregoli (b. 2003)
Kaia James (b. 2006)