best film:   Million Dollar Baby is a worthy film to have as any actor’s best film. Clint Eastwood certainly had an impressive creative stretch run from 2003 to 2006 with his trademark desaturated blue, green and gray hues.  She is the lead actor and excellent in a masterpiece (even if it is a weaker one) – so this is a category of strength for Swank at this point on the list. Boys Don’t Cry (1999) most definitely takes the subsequent spot here.


Swank as Maggie Fitzgerald – a great addition to the lineage of exceptional performances from actors portraying boxers or ex-boxers


best performance:   Million Dollar Baby takes this category as well but Swank’s work in Boys Don’t Cry is much closer in terms of performance from Swank than the overall film. Both films boast a trio of ridiculously impressive acting performances. In Boys Don’t Cry, Swank is flanked by indie film goddess Chloë Sevigny and Peter Sarsgaard. It is none other than Eastwood himself and veteran Morgan Freeman who support Swank in the 2004 masterpiece. It is a compliment to Swank that she is able to lead actors of this caliber in both films.


stylistic innovations/traits:   Hilary Swank was born in Lincoln, Nebraska – just like her character Brandon Teena in 1999’s Boys Don’t Cry. This is undoubtedly the film and performance that put the young actor (twenty-five (25) at the time in 1999) on the map. Swank capitalized on her breakthrough with a rock-solid supporting role in Christopher Nolan’s Insomnia (2002) and then of course her peak (and yet another lead actress Oscar win) in 2004’s Million Dollar Baby. Swank’s best four performances (and four of the five overall archiveable films) come between the 1999-2004 stretch. Her defining characteristic is her grit – she plays characters that often take an emotional and physical beating. Swank is clearly no ex-model beauty queen – and her untraditional (by Hollywood’s crazy standards) looks may hurt her in terms of the longevity of her career – it obviously did not hurt her when turning out these two iconic characters.


the buzz in 1999 was “is this an actor or a real person?” – which is always a good sign – for Swank’s revelatory performance in Boys Don’t Cry


directors worked with:  Christopher Nolan (1), Clint Eastwood (1), Steven Soderbergh (1)


sandwiched between her two Oscar wins, Swank here in a smaller, but very decent role opposite Robin Williams and Al Pacino in Insomnia (2002)


top five performances:

  1. Million Dollar Baby
  2. Boys Don’t Cry
  3. Insomnia
  4. The Gift
  5. Logan Lucky


archiveable films

1999- Boys Don’t Cry
2000- The Gift
2002- Insomnia
2004- Million Dollar Baby
2017- Logan Lucky