Suggestions by @itsgrapes_exe

Nathan Salstone

as Tobias Ragg in Sweeney Todd

Score: +1

Kate Winslet

as Mrs. Nellie Lovett in Sweeney Todd

Score: +2

Raúl Esparza

as Sweeney Todd in Sweeney Todd

Score: +1

Steven Spielberg

as Director in Sweeney Todd: The Demon Barber of Fleet Street

Score: +1

Andrew Keenan-Bolger

as Giuseppe Zangara in Assassins

Score: +1

John Bolton

as Charles Guiteau in Assassins (musical)

Score: +1

Jay Armstrong Johnson

as Winifred Sanderson in Celebrities as Halloween Costumes

Score: 0

John Bolton

as Charles Guiteau in Assassins

Score: +1

Emmett Forrest

as Harvard University in Fictional Characters sorted by Real Colleges

Score: +1

Jay Gatsby

as University of Oxford in Fictional Characters sorted by Real Colleges

Score: +1

Keith Leak Jr.

as Mitch Mahoney in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Damien Haas

as Leaf Coneybear in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Angela Giarratana

as Olive Ostrovsky in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +2

Shayne Topp

as William Barfee in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Courtney Miller

as Logainne Schwartzandgrubenierre in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Olivia Sui

as Marcy Park in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Chanse McCrary

as Chip Tolentino in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Anthony Padilla

as Jesus in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Amanda Lehan-Canto

as Rona Lisa Peretti in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1

Ian Hecox

as Vice Principal Panch in Smosh Presents: The 25th Annual Putnam County Spelling Bee

Score: +1