Suggestions by @Mrsticky

Ryan Gosling

as Harry Osborn in The Amazing Spider-Man (2002-2010)

Kian Egan

as Peter Parker in The Amazing Spider-Man (2002-2010)

Alexis Bledel

as Mary Jane Watson in The Amazing Spider-Man (2002-2010)

Stephen Gately

as Harry Osborn in Spider Man 2004

Hugh Laurie

as Dr Curt Connors (2004-2007) in Spider-Man (2002-2007-2012-2014-2017-2021)

Amanda Bynes

as Mary Jane Watson (2002-2007) in Spider-Man (2002-2007-2012-2014-2017-2021)

Eminem

as Max Dillon (2014,2021) in Spider-Man (2002-2007-2012-2014-2017-2021)

Sebastian Stan

as Harry Osborn (2014) in Spider-Man (2002-2007-2012-2014-2017-2021)

Jensen Ackles

as Eddie Brock (2018-2021) in Spider-Man (2002-2007-2012-2014-2017-2021)

Duncan James

as Eddie Brock (2007) in Spider-Man (2002-2007-2012-2014-2017-2021)

Lee Ryan

as Peter Parker (2002-2007,2021) in Spider-Man (2002-2007-2012-2014-2017-2021)

Lee Ryan

as Peter Parker (2012-2017,2021) in Spider-Man (2002-2007-2012-2014-2017-2021)

Eli Marienthal

as Peter Parker in Spider-Man (2002-2007-2012-2014-2017-2021)

Drake Bell

as Peter Parker in Spider-Man (2002-2007-2012-2014-2017-2021)

Emily Rudd

as Michelle Jones in Spider-Man (2002-2007-2012-2014-2017-2021)

Oded Fehr

as Tony Stark (2017-2019) in Spider-Man (2002-2007-2012-2014-2017-2021)

Elisha Cuthbert

as Gwen Stacy (2007) in Spider-Man (2002-2007-2012-2014-2017-2021)

Wes Bentley

as Peter Parker (2002-2007,2021) in Spider-Man (2002-2007-2012-2014-2017-2021)

Larisa Oleynik

as Mary Jane Watson (2002-2007) in Spider-Man (2002-2007-2012-2014-2017-2021)

Joseph Gordon-Levitt

as Peter Parker (2002-2007,2021) in Spider-Man (2002-2007-2012-2014-2017-2021)