- Bette Midler starred in Hocus Pocus (1993) alongside Kathy Najimy.
- Kathy Jajimy was the loud, larger-than-life Sister Mary Patrick in Sister Act (1992), which also starred Whoopi Goldberg.
- Whoopi Goldberg was in Made in America (1993) with Will Smith.
- Will Smith was in Wild Wild West (1999) with Salma Hayek.
- Salma Hayek was in From Dusk Till Dawn (1996) with George Clooney.
- George Clooney was in Ocean's Eleven (2001) with Brad Pitt.
- Brad Pitt was in Mr and Mrs Smith (2005) with Angelina Jolie
Alternatively, another route I thought of a couple of days later:
- Bette Midler starred in Hocus Pocus (1993) alongside Kathy Najimy.
- Kathy Jajimy was the loud, larger-than-life Sister Mary Patrick in Sister Act (1992), with Harvey Keitel.
- Harvey Keitel was in Thelma and Louise (1991) which had a young Brad Pitt.
- Brad Pitt was in Mr and Mrs Smith (2005) with Angelina Jolie.
