Now that Oscar season is upon us, a deluge of commentary is sure to crop up on the web about the various disappointments: the Black actors who weren’t nominated, those who were nominated but weren’t deserving, and the default (legitimate) argument that there just aren’t enough quality roles for Black actors.

We thought it would be fun to take a few steps back and look at the past 20+ years of Black Oscar winners and evaluate whether an Oscar is all that it’s cracked up to be, especially if you’re black in Hollywood. What is it really worth in terms of a Black actor’s career? What kind of political minefield must one tap dance on? Does it guarantee more money? Are Black actors welcomed into the coveted A-List? And perhaps most important: Will said Black Oscar winner be working in the next two, three years? And if so, will it be Oscar-caliber work or the same old stereotypes?

In the last two decades, give or take, we’ve seen the largest number of Black Oscar winners. Ten to be exact: five men and five women. Regrettably not equally distributed in categories of leading and supporting roles or along gender lines. As we know Black actresses have a harder time winning and getting roles as leading ladies.

Let’s take a close look at the 10 Oscar winners, examining whether the Oscar has made a difference, if at all, to their careers.

Whoopi Goldberg won Best Supporting Actress in 1990 for playing Oda Mae Brown in Ghost making her the second African American woman to win in the category of Best Supporting Actress. Her predecessor is Hattie McDaniel who won for playing Mammy in Gone With the Wind (1939). Few actors—Black or white—can hold a candle to Ms. Goldberg. Disappointingly, however, her best work happened in the 1980s culminating with Ghost (1990). Her biggest films Post-Oscar include Sister Act (1992), Sarafina (1992) and Corrina, Corrina (1994). Part of the disappointment is that Hollywood didn’t seem to know what to do with Ms. Goldberg who is both hysterically funny and a dramatic force on screen. In several previous interviews, Ms. Goldberg talked openly about directors giving her a hard time because of her looks. On the whole, Ms. Goldberg’s Oscar seems inconsequential as she hasn’t headlined a major film since Sister Act 2 (1992) and she’s gone into semi-retirement making appearances on television shows and becoming a talking head on the talk show, The View.