Ah, reunions. They’re those milestones of aging that both appeal to our curiosity and make us cower in fear. From failed romances to unresolved conflicts, it's all shoved back into the spotlight. Not to mention the weight gain and crow's feet.

Case in point is this week's The Best Man Holiday, which reunites the cast of 1999's The Best Man for cringe-worthy festivities full of rekindled romances and rivalries. What other reunion films hit that sweet spot of nostalgia, humor and regret?

By Tara Bennett

Romy and Michelle's High School Reunion

Bubble-headed BFFs Romy (Mira Sorvino) and Michelle (Lisa Kudrow) survived being tortured in high school together and stayed joined at the hip for a decade. With their upcoming high school reunion, they realize they haven’t accomplished much so they set about getting impressive to upstage the jerks they left behind. Often hilarious because of the excellent chemistry between Sorvino and Kudrow, the clueless ladies navigate vulnerability and stupidity with heart.

Grosse Pointe Blank

A truly delicious black comedy, Martin Blank (John Cusack) is a hit man suffering a midlife occupational crisis just in time for his 10-year high school reunion. Despite an assassination that hasn’t been completed, he packs up for Michigan and reunites with the woman who got away, Debi Newberry (played perfectly by Minnie Driver), and the friends who still consider him a local icon. It features an incredible script (cowritten by Cusack), soundtrack and performances; a gold-standard reunion movie.

Beautiful Girls

Timothy Hutton plays Willie Conway, a bar pianist who is at a life crossroads when he returns home to his blue-collar neighborhood. Pondering marriage and a career change, Willie gets caught up in the drama of his old friends and their equally complicated and stalled lives. Girls skews heavily on the romantic side, but Hutton leads a really talented cast including Natalie Portman, Matt Dillon, Uma Thurman and more, who get you invested in their small-town lives.

The Big Chill

When people talk about the reunion genre, The Big Chill is one of the first movies always offered as one of the best. Thirty years old this year, the film explores the relationships of seven college friends who come together for the funeral of one of their circle. Actually heavily inspired by director John Sayles’ The Return of the Secaucus Seven (see that one too), The Big Chill is remembered for its wickedly talented ensemble featuring Glenn Close, Kevin Kline, William Hurt, JoBeth Williams and even dead Kevin Costner for a millisecond.

The Blues Brothers

When Jake Blues (John Belushi) gets out of Joliet prison he gets picked up by his brother, Elwood (Dan Aykroyd), and their entire life’s purpose becomes “putting the band back together.” As they terrorize the suburbs and city of Chicago, the pair collects their former bandmates for a concert to prevent their Catholic halfway home from being shut down. The Blues Brothers is the cautionary tale of reuniting with your past, but it’s a classic.

The Wood

In The Wood nostalgia gets framed by a writer in the present looking back at his childhood friends on the eve of one of their weddings. Mike, Slim and Roland get their lives told in flashback while a case of cold feet threatens to ruin the wedding day. Both a coming-of-age story and an exploration of friendship and love through the years, the narrative device lets the past boost the reunion in the present.

Peter’s Friends

For Anglophiles, Peter’s Friends is sort of the Brit take on The Big Chill. Kenneth Branagh directed this ensemble piece back when he was still married to Emma Thompson. Six former college friends and some new significant others come together for a New Years Eve weekend reunion where the past and the present collide. Hugh Laurie, Stephen Fry, Imelda Staunton and even Rita Rudner give some pretty great performances.

A Mighty Wind

Christopher Guest’s mockumentary about the big names in folk music coming together again for a public television special has something for everyone. There’s plenty of comedic weirdness surrounding the characters, especially Eugene Levy’s super-baked Mitch Cohen, a great original soundtrack, and genuine heart as these alternative singers of a bygone era come together to celebrate their song books.

Garden State

Zach Braff’s feature directorial debut is too navel-gazing whiny for some, but at its heart there’s a poignant exploration of how going back home can free your present demons. Braff’s Andrew Largeman is a guy in his 20s who spent the majority of his youth on antidepressants. Now a struggling actor in L.A., he returns to New Jersey for his mom’s funeral and confronts his adolescence via friends he reconnects with in the area. It boasts a terrific soundtrack and a stellar performance by Natalie Portman too.

Young Adult

Definitely not a movie for everyone, but Charlize Theron knocks it out of the park as Mavis Gary, a textbook narcissist who writer semi-successful YA books. Self-obsessed and spiraling, she returns home to Minnesota to try to seduce her former high school love from his new fiancée. She hits all of her old haunts and even reconnects with high school “loser” Matt Freehauf (a brilliant Patton Oswald), who is the only person who sees her as the broken person she’s become.