Tipsy Toasts And Family Feuds: These Are Holly Montag's Most Unforgettable 'Hills' Moments

Before Heidi's big sister becomes a mom, take a look back at her Tinseltown adventures.

These days, Holly Montag is happily married to hubby Richie Wilson, and the couple is excitedly awaiting the birth of their first child. But a few years back, Heidi Montag's sibling was living the "Hills" dream -- and was known for drumming up a bit of drama along the way. Exhibit A: the face below, after making an awkward speech at Speidi's pre-wedding festivities and spilling some shmutz on her sis' bag:

As Holly's due date approaches and she gets thisclose to beginning her brand-new life as a proud mommy to Baby Isaiah -- that's right, it's a boy! -- we're taking a fond look back at her pre-parenthood adventures in SoCal:

  • Roommate tension

    Holly decided to leave her Colorado roots for the City of Angels -- and shortly after her Tinseltown arrival, she relied on Heidi and Spencer for some temporary lodging. But the longer-than-expected stay began to grate on Spence's nerves, which in turn caused a slow-burning rift between the sisters.

  • A controversial lunch

    The older Montag enjoyed a cordial meal with Lauren, during which Heidi was the main topic of conversation. The friendly meeting understandably drummed up a bit of emotion for Heidi, and the sisters' issues only mounted from there.

  • Going, going...gone.

    Heids was forced to make a difficult decision: allow Holly to continue to crash at her apartment or deal with Spencer moving on out. Ultimately, Holls packed her bags -- and the connection between the ladies began to crumble.

  • Interesting roomie combo

    When Holly had nowhere else to go, she crashed at the abode of her sis' adversary. Heidi soon caught wind of the unique housing sitch and blamed Spencer for her damaged bond with H.

  • An unforgettable rehearsal dinner toast -- that ruined her sis' purse

    H's bizarre, booze-infused speech was certainly the highlight before Speidi's big day. Staining Heidi's clutch and yelling inappropriate comments about her future bro-in-law? That was just the uncomfortable icing on the cake.

  • An impromptu intervention

    Heidi and lil Stephanie Pratt worried for Holly's well-being after she got a wee bit intoxicated during a gathering. But the gals' efforts to talk to H about her behavior were unsuccessful and only created a wider wedge between the Montags.

  • "I feel like she's gone forever"

    Talk about a heartbreaking sit-down with all the "Hills" girls. The crew -- led by Hol and Steph -- made the difficult decision that they needed to cut Speidi out of their lives...for good.

  • Missing Heidi

    Even though Holly and her mom Darlene weren't in contact with Heidi, they deeply missed her. This emotional scene marked Holls' final cameo on the hit MTV series.

+ What's your favorite Holly incident? Share your memories in the comments below, and offer your well wishes before Baby I's highly anticipated arrival!