The pod hits triple digits, and Sam immediately blows the budget - dropping $663 on hotel laundry in New York. That fiasco sets the tone for an episode packed with shaky quarterfinal predictions, a surprisingly deep dive into life choices, and a full Round 4 recap.

From Anna Wintour lurking courtside to Jason Biggs randomly popping up, the celebrity sightings nearly stole the show… nearly. The guys break down Felix’s revival, Alcaraz’s shot-of-the-year candidate, Novak’s effortless cruise, and Fritz’s eternal struggle against him.

On the women’s side, Iga keeps steamrolling, Osaka looks dangerous again after taking out Coco, Pegula is gliding quietly under the radar, and Krejcikova delivered what might be the match of the tournament.

Things wrap up with one of the wildest Life Advice questions yet. The guys dish out surprisingly heartfelt guidance—sandwiched between trash talk about their bracket challenge and scheming over who’s doomed to write and sing a jingle. Chaotic, sharp, and accidentally sincere… basically the perfect 100th episode.

00:00 Intro to Our 100th Show!

00:37 Dry Cleaning in New York

02:22 Celebrity Sightings

03:27 Recap of Round of 16 Matches

05:27 Felix / Musetti Surprising Performances

09:57 Novak's Dominant Form

11:52 Alcaraz's Shot of the Year

12:54 Quarterfinals Preview / Predictions

15:17 Women's Quarterfinal Highlights

17:35 Match of the Tournament: Krejcikova vs. Townsend

19:21 Osaka vs. Coco Gauff Analysis

23:27 Life Advice Segment

25:56 Bracket Challenge Update and Goodbye!