Heikki Kovalainen set the pace under dry conditions in Monaco on Saturday morning, moments before losing it and crashing out.
The Finn, who at the time was quicker than Lewis Hamilton and Kimi Raikkonen, still managed to finish the session at the top of the timesheets as the rain came down soon after his crash, forcing the drivers to lap roughly ten seconds slower than usual.
With the threat of rain overhead the drivers were quick to take to the track, with everyone barring the Toyotas and Kimi Raikkonen completing an installation lap within the first five minutes.
Massa went on to post the first competitive lap time of the session, a 1:23.729. The Brazilian shaved over two seconds off his time on the next lap.
Nico Rosberg and Kazuki Nakajima slotted in behind him on the timesheets as other drivers came out on track to set their first lap times of the morning, while those at the top continued to lower the benchmark.
Kimi Raikkonen jumped to the top with a 1:19.204 only to lose out to Massa, who clocked a 1:17.691. The Brazilian, though, was passed by Raikkonen then Heikki Kovalainen and then Lewis Hamilton.
The rain came down lightly 20 minutes into the session, sending half the field back into the pits.
Mark Webber, though, stayed out taking sixth place while Adrian Sutil moved up to seventh behind the Red Bull driver.
Kovalainen, using the super soft tyres, took the P1 slot off his team-mate only to lose control on the following lap when he hit the wall at the exit of the Swimming Pool.
The light tap damaged his rear right tyre, putting the Finn isn't a spin and out of the session. It also brought out the red flags for three minutes.
Once restarted the drivers were slow to take to the track as the wet conditions made for a trying time. Renault, though, were the first out as Fernando Alonso and Nelson Piquet Jr put in some wet running.
More drivers hit the track and even though the rain stopped with 15 minutes on the clock the wet surface meant lap times were significantly slower with Jenson Button, the quickest driver in the wet, lapping in the 1:31s.
The rain returned for the last five minutes of practice with the Ferrari drivers and Robert Kubica proving to be the quickest in the wet. Massa showed impressive pace, setting a 1:29.997 in the wet while Raikkonen went even quicker with a 1:27.937. Kubica, though, beat both their times with a 1:26.921.
However, the BMW driver's wet lap time was a full ten seconds off the pace set by Kovalainen earlier in dry conditions.
Times
01 H. Kovalainen McLaren 1:16.567 11 laps
02 L. Hamilton McLaren 1:17.084 14 laps
03 K. Räikkönen Ferrari 1:17.177 20 laps
04 N. Rosberg Williams 1:17.503 26 laps
05 R. Kubica BMW 1:17.687 22 laps
06 F. Massa Ferrari 1:17.691 26 laps
07 M. Webber Red Bull 1:17.856 21 laps
08 A. Sutil Force India F1 1:17.883 23 laps
09 K. Nakajima Williams 1:18.147 25 laps
10 J. Button Honda 1:18.225 27 laps
11 S. Bourdais Scuderia Toro Rosso 1:18.367 16 laps
12 T. Glock Toyota 1:18.424 25 laps
13 R. Barrichello Honda 1:18.455 18 laps
14 N. Piquet jr. Renault 1:18.615 24 laps
15 S. Vettel Scuderia Toro Rosso 1:18.651 28 laps
16 F. Alonso Renault 1:18.795 23 laps
17 J. Trulli Toyota 1:18.858 24 laps
18 N. Heidfeld BMW 1:19.024 22 laps
19 G. Fisichella Force India F1 1:19.131 10 laps
20 D. Coulthard Red Bull 1:20.805 16 laps
